5-Hydroxylysine (BioDeep_00000001264)

 

Secondary id: BioDeep_00000398026

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 Volatile Flavor Compounds natural product


代谢物信息卡片


alpha,epsilon-Diamino-delta-hydroxycaproic acid

化学式: C6H14N2O3 (162.1004374)
中文名称: 5-羟基-DL-赖氨酸 盐酸盐, 5-羟基赖氨酸
谱图信息: 最多检出来源 Homo sapiens(feces) 0.06%

分子结构信息

SMILES: C(CC(C(=O)O)N)C(CN)O
InChI: InChI=1S/C6H14N2O3/c7-3-4(9)1-2-5(8)6(10)11/h4-5,9H,1-3,7-8H2,(H,10,11)

描述信息

5-Hydroxylysine (Hyl), also known as hydroxylysine or 5-Hydroxy-L-lysine, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. 5-Hydroxylysine is a hydroxylated derivative of the amino acid lysine that is present in certain collagens, the chief structural protein of mammalian skin and connective tissue. 5-Hydroxylysine arises from a post-translational hydroxy modification of lysine and is biosynthesized from lysine via oxidation by lysyl hydroxylase enzymes. 5-Hydroxylysine can then undergo further modification by glycosylation, giving rise to galactosyl hydroxylysine (GH) and glucosylgalactosyl hydroxylysine (GGH). These glycosylated forms of hydroxylysine contribute to collagen’s unusual toughness and resiliency. The monoglycosylated, galactosyl-hydroxylysine is enriched in bone compared with the disaccharide form, glucosyl-galactosyl-hydroxylysine, which is the major form in skin. 5-Hydroxylysine exists in all eukaryotes, ranging from yeast to humans. It was first discovered in 1921 by Donald Van Slyke. Free forms of hydroxylysine arise through proteolytic degradation of collagen. Urinary excretion of 5-Hydroxylysine and its glycosides can be used as an index of collagen degradation, with high levels being indicative of more rapid or extensive collagen degradation (often seen in patients with thermal burns, Pagets disease of bone or hyperphosphatasia) (PMID: 404321).
One of the natural protein-bound amino acids. Occurs free in plant tissues, e.g. Medicago sativa (alfalfa)

同义名列表

36 个代谢物同义名

alpha,epsilon-Diamino-delta-hydroxycaproic acid; a,epsilon-Diamino-delta-hydroxycaproic acid; alpha,epsilon-Diamino-delta-hydroxycaproate; (2S,5R)-2,6-Diamino-5-hydroxyhexanoic acid; Procollagen L-erythro-5-hydroxy-L-lysine; a,epsilon-diamino-δ-hydroxycaproic acid; Α,epsilon-diamino-δ-hydroxycaproic acid; a,epsilon-Diamino-delta-hydroxycaproate; (2S,5R)-2,6-diamino-5-Hydroxyhexanoate; Α,epsilon-diamino-δ-hydroxycaproate; a,epsilon-diamino-δ-hydroxycaproate; 2,6 Diamino 5 hydroxyhexanoic acid; 2,6-Diamino-5-hydroxyhexanoic acid; Procollagen 5-hydroxy-L-lysine; erythro-5-Hydroxy-L-lysine; L-Erythro-5-hydroxylysine; L-Normal-5-hydroxylysine; (5R)-5-Hydroxy-L-lysine; (2S,5R)-5-Hydroxylysine; delta-Hydroxy-L-lysine; delta-DL-Hydroxylysine; L-delta-Hydroxylysine; delta-Hydroxylysine; D-Hydroxy-L-lysine; 5-Hydroxy-L-lysine; L-D-Hydroxylysine; Lysine, 5 hydroxy; 5-Hydroxy-lysine; 5 Hydroxylysine; 5-hydroxylysine; L-hydroxylysine; D-Hydroxylysine; Hydroxy-lysine; Hydroxylysine; 5-Hydroxylysine; L-Hydroxylysine



数据库引用编号

25 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

46 个相关的代谢反应过程信息。

Reactome(45)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

11 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Dang Dang Wang, Guang Fu Tang, Yuan Yuan Li, Jun Jian Yu, Xin Jian Lei, Yang Chun Cao, Jun Hu Yao. Differences in serum metabolome profile explain individual variation in growth performance of young goats. Journal of proteomics. 2023 Jul; 288(?):104982. doi: 10.1016/j.jprot.2023.104982. [PMID: 37532014]
  • Shangqing Li, Guorong Lyu, Shaohui Li, Hainan Yang, Yiru Yang. Metabolic characterization of amniotic fluid of fetuses with isolated choroid plexus cyst. Journal of perinatal medicine. 2022 Oct; 50(8):1100-1106. doi: 10.1515/jpm-2022-0028. [PMID: 35607760]
  • Nina Patel, Philippa Mills, James Davison, Maureen Cleary, Paul Gissen, Blerida Banushi, Ivan Doykov, Megan Dorman, Kevin Mills, Wendy E Heywood. Free urinary glycosylated hydroxylysine as an indicator of altered collagen degradation in the mucopolysaccharidoses. Journal of inherited metabolic disease. 2020 03; 43(2):309-317. doi: 10.1002/jimd.12166. [PMID: 31452203]
  • Michael Behringer, Johannes Caspar Konrad Montag, Yvonne Kilian, Phil Heaton, Joachim Mester. Polyamines, myosin heavy chains, and collagen specific amino acids after a repeated bout of eccentric exercise. Research in sports medicine (Print). 2016 Jul; 24(3):287-97. doi: 10.1080/15438627.2016.1202830. [PMID: 27379471]
  • O V Zaitseva, S G Shandrenko, M M Veliky. Biochemical markers of bone collagen type I metabolism. Ukrainian biochemical journal. 2015 Jan; 87(1):21-32. doi: 10.15407/ubj87.01.021. [PMID: 26036128]
  • Peter Bross, Jane B Frederiksen, Anne S Bie, Jakob Hansen, Johan Palmfeldt, Marit N Nielsen, Morten Duno, Allan M Lund, Ernst Christensen. Heterozygosity for an in-frame deletion causes glutaryl-CoA dehydrogenase deficiency in a patient detected by newborn screening: investigation of the effect of the mutant allele. Journal of inherited metabolic disease. 2012 Sep; 35(5):787-96. doi: 10.1007/s10545-011-9437-y. [PMID: 22231382]
  • Krista Viau, Sharon L Ernst, Rena J Vanzo, Lorenzo D Botto, Marzia Pasquali, Nicola Longo. Glutaric acidemia type 1: outcomes before and after expanded newborn screening. Molecular genetics and metabolism. 2012 Aug; 106(4):430-8. doi: 10.1016/j.ymgme.2012.05.024. [PMID: 22728054]
  • Miquel Rojas-Cherto, Julio E Peironcely, Piotr T Kasper, Justin J J van der Hooft, Ric C H de Vos, Rob Vreeken, Thomas Hankemeier, Theo Reijmers. Metabolite identification using automated comparison of high-resolution multistage mass spectral trees. Analytical chemistry. 2012 Jul; 84(13):5524-34. doi: 10.1021/ac2034216. [PMID: 22612383]
  • Valentina Citton, Alberto Burlina, Claudio Baracchini, Massimo Gallucci, Alessia Catalucci, Sandro Dal Pos, Alessandro Burlina, Renzo Manara. Apparent diffusion coefficient restriction in the white matter: going beyond acute brain territorial ischemia. Insights into imaging. 2012 Apr; 3(2):155-64. doi: 10.1007/s13244-011-0114-3. [PMID: 22696041]
  • Joanna Stafiej, Grażyna Malukiewicz, Hanna Lesiewska-Junk, Danuta Rość, Karolina Kaźmierczak. Endothelial cell markers in patients with pseudoexfoliation syndrome. TheScientificWorldJournal. 2012; 2012(?):863949. doi: 10.1100/2012/863949. [PMID: 22593709]
  • Petteri Nieminen, Tommi Paakkonen, Harri Eerilä, Katri Puukka, Joakim Riikonen, Vesa-Pekka Lehto, Anne-Mari Mustonen. Freezing tolerance and low molecular weight cryoprotectants in an invasive parasitic fly, the deer ked (Lipoptena cervi). Journal of experimental zoology. Part A, Ecological genetics and physiology. 2012 Jan; 317(1):1-8. doi: 10.1002/jez.722. [PMID: 22076947]
  • Muhammad Sughis, Joris Penders, Vincent Haufroid, Benoit Nemery, Tim S Nawrot. Bone resorption and environmental exposure to cadmium in children: a cross--sectional study. Environmental health : a global access science source. 2011 Dec; 10(?):104. doi: 10.1186/1476-069x-10-104. [PMID: 22151692]
  • Marianne Rohrbach, Anthony Vandersteen, Uluç Yiş, Gul Serdaroglu, Esra Ataman, Maya Chopra, Sixto Garcia, Kristi Jones, Ariana Kariminejad, Marius Kraenzlin, Carlo Marcelis, Matthias Baumgartner, Cecilia Giunta. Phenotypic variability of the kyphoscoliotic type of Ehlers-Danlos syndrome (EDS VIA): clinical, molecular and biochemical delineation. Orphanet journal of rare diseases. 2011 Jun; 6(?):46. doi: 10.1186/1750-1172-6-46. [PMID: 21699693]
  • Katja Brauburger, Gerhard Burckhardt, Birgitta C Burckhardt. The sodium-dependent di- and tricarboxylate transporter, NaCT, is not responsible for the uptake of D-, L-2-hydroxyglutarate and 3-hydroxyglutarate into neurons. Journal of inherited metabolic disease. 2011 Apr; 34(2):477-82. doi: 10.1007/s10545-010-9268-2. [PMID: 21264516]
  • Chie Shimmura, Shiro Suda, Kenji J Tsuchiya, Kenji Hashimoto, Koji Ohno, Hideo Matsuzaki, Keiko Iwata, Kaori Matsumoto, Tomoyasu Wakuda, Yosuke Kameno, Katsuaki Suzuki, Masatsugu Tsujii, Kazuhiko Nakamura, Nori Takei, Norio Mori. Alteration of plasma glutamate and glutamine levels in children with high-functioning autism. PloS one. 2011; 6(10):e25340. doi: 10.1371/journal.pone.0025340. [PMID: 21998651]
  • Sten Andersen, Harald Mischak, Petra Zürbig, Hans-Henrik Parving, Peter Rossing. Urinary proteome analysis enables assessment of renoprotective treatment in type 2 diabetic patients with microalbuminuria. BMC nephrology. 2010 Nov; 11(?):29. doi: 10.1186/1471-2369-11-29. [PMID: 21040538]
  • David M Maahs, Justyna Siwy, Angel Argilés, Marie Cerna, Christian Delles, Anna F Dominiczak, Nathalie Gayrard, Alexander Iphöfer, Lothar Jänsch, George Jerums, Karel Medek, Harald Mischak, Gerjan J Navis, Johannes M Roob, Kasper Rossing, Peter Rossing, Ivan Rychlík, Eric Schiffer, Roland E Schmieder, Thomas C Wascher, Brigitte M Winklhofer-Roob, Lukas U Zimmerli, Petra Zürbig, Janet K Snell-Bergeon. Urinary collagen fragments are significantly altered in diabetes: a link to pathophysiology. PloS one. 2010 Sep; 5(9):. doi: 10.1371/journal.pone.0013051. [PMID: 20927192]
  • Hussein A Algahtani, Abduljaleel P Abdu, Imad M Khojah, Ali M Al-Khathaami. Inability to walk due to scurvy: A forgotten disease. Annals of Saudi medicine. 2010 Jul; 30(4):325-8. doi: 10.4103/0256-4947.65266. [PMID: 20622353]
  • Theo H M Smits, Sebastian Jaenicke, Fabio Rezzonico, Tim Kamber, Alexander Goesmann, Jürg E Frey, Brion Duffy. Complete genome sequence of the fire blight pathogen Erwinia pyrifoliae DSM 12163T and comparative genomic insights into plant pathogenicity. BMC genomics. 2010 Jan; 11(?):2. doi: 10.1186/1471-2164-11-2. [PMID: 20047678]
  • I Höliner, B Simma, A Reiter, J O Sass, J Zschocke, Martina Huemer. Compliance to clinical guidelines determines outcome in glutaric aciduria type I in the era of newborn screening. Klinische Padiatrie. 2010 Jan; 222(1):35-7. doi: 10.1055/s-0029-1239525. [PMID: 20084589]
  • Masashi Niimi, Lian Tao, Shi-Hua Lin, Jun Yin, Xiaoyun Wu, Hiroyuki Fukui, Junichi Kambayashi, Jianping Ye, Bing Sun. Involvement of an alternatively spliced mitochondrial oxodicarboxylate carrier in adipogenesis in 3T3-L1 cells. Journal of biomedical science. 2009 Oct; 16(?):92. doi: 10.1186/1423-0127-16-92. [PMID: 19825180]
  • Gilbert L Hendricks, Jill A Hadley, Susan M Krzysik-Walker, K Sandeep Prabhu, Regina Vasilatos-Younken, Ramesh Ramachandran. Unique profile of chicken adiponectin, a predominantly heavy molecular weight multimer, and relationship to visceral adiposity. Endocrinology. 2009 Jul; 150(7):3092-100. doi: 10.1210/en.2008-1558. [PMID: 19299452]
  • P Bergmann, J-J Body, S Boonen, Y Boutsen, J-P Devogelaer, S Goemaere, J-M Kaufman, J-Y Reginster, V Gangji. Evidence-based guidelines for the use of biochemical markers of bone turnover in the selection and monitoring of bisphosphonate treatment in osteoporosis: a consensus document of the Belgian Bone Club. International journal of clinical practice. 2009 Jan; 63(1):19-26. doi: 10.1111/j.1742-1241.2008.01911.x. [PMID: 19125989]
  • Oliver Fricke, Christof Land, Ralf Beccard, Oliver Semler, Angelika Stabrey, Eckhard Schoenau. The relationship between body composition and the urinary excretion of deoxypyridinoline and galactosyl-hydroxylysine in children and adolescents. Journal of bone and mineral metabolism. 2009; 27(6):689-97. doi: 10.1007/s00774-009-0083-5. [PMID: 19526303]
  • Stephane Walrand, Eleni Chiotelli, Florence Noirt, Sandrine Mwewa, Taous Lassel. Consumption of a functional fermented milk containing collagen hydrolysate improves the concentration of collagen-specific amino acids in plasma. Journal of agricultural and food chemistry. 2008 Sep; 56(17):7790-5. doi: 10.1021/jf800691f. [PMID: 18707117]
  • A A-B Badawy, C J Morgan, J A Turner. Application of the Phenomenex EZ:faasttrade mark amino acid analysis kit for rapid gas-chromatographic determination of concentrations of plasma tryptophan and its brain uptake competitors. Amino acids. 2008 May; 34(4):587-96. doi: 10.1007/s00726-007-0012-7. [PMID: 18071842]
  • Trifon Tofas, Athanasios Z Jamurtas, Ioannis Fatouros, Michalis G Nikolaidis, Yiannis Koutedakis, Efstathios A Sinouris, Nickoletta Papageorgakopoulou, Dimitrios A Theocharis. Plyometric exercise increases serum indices of muscle damage and collagen breakdown. Journal of strength and conditioning research. 2008 Mar; 22(2):490-6. doi: 10.1519/jsc.0b013e31816605a0. [PMID: 18550965]
  • E de Luis, J Larrache, R García-Eulate, J Narbona García, J L Zubieta. [Neuroradiologic findings of glutaric aciduria type I]. Revista de medicina de la Universidad de Navarra. 2007 Jul; 51(3):9-12. doi: . [PMID: 18183780]
  • Antti M Salo, Laura Sipilä, Raija Sormunen, Heli Ruotsalainen, Seppo Vainio, Raili Myllylä. The lysyl hydroxylase isoforms are widely expressed during mouse embryogenesis, but obtain tissue- and cell-specific patterns in the adult. Matrix biology : journal of the International Society for Matrix Biology. 2006 Oct; 25(8):475-83. doi: 10.1016/j.matbio.2006.08.260. [PMID: 16996725]
  • Antti M Salo, Chunguang Wang, Laura Sipilä, Raija Sormunen, Miia Vapola, Päivi Kervinen, Heli Ruotsalainen, Jari Heikkinen, Raili Myllylä. Lysyl hydroxylase 3 (LH3) modifies proteins in the extracellular space, a novel mechanism for matrix remodeling. Journal of cellular physiology. 2006 Jun; 207(3):644-53. doi: 10.1002/jcp.20596. [PMID: 16447251]
  • Gary L Hedlund, Nicola Longo, Marzia Pasquali. Glutaric acidemia type 1. American journal of medical genetics. Part C, Seminars in medical genetics. 2006 May; 142C(2):86-94. doi: 10.1002/ajmg.c.30088. [PMID: 16602100]
  • T Ahsan, F Harwood, K B McGowan, D Amiel, R L Sah. Kinetics of collagen crosslinking in adult bovine articular cartilage. Osteoarthritis and cartilage. 2005 Aug; 13(8):709-15. doi: 10.1016/j.joca.2005.03.005. [PMID: 16043034]
  • Shyama Chatterjee, Gunther Vrolix, Inge Depoortere, Theo Peeters, Eric Van Marck. The therapeutic effect of the neuropeptide hormone somatostatin on Schistosoma mansoni caused liver fibrosis. BMC infectious diseases. 2005 Jun; 5(?):45. doi: 10.1186/1471-2334-5-45. [PMID: 15949036]
  • F Pagani, C M Francucci, L Moro. Markers of bone turnover: biochemical and clinical perspectives. Journal of endocrinological investigation. 2005; 28(10 Suppl):8-13. doi: NULL. [PMID: 16550716]
  • Linda C Walker, Mayra A Overstreet, Heather N Yeowell. Tissue-specific expression and regulation of the alternatively-spliced forms of lysyl hydroxylase 2 (LH2) in human kidney cells and skin fibroblasts. Matrix biology : journal of the International Society for Matrix Biology. 2005 Jan; 23(8):515-23. doi: 10.1016/j.matbio.2004.11.002. [PMID: 15694128]
  • Baris Simsek, Ozgül Karacaer, Inci Karaca. Urine products of bone breakdown as markers of bone resorption and clinical usefulness of urinary hydroxyproline: an overview. Chinese medical journal. 2004 Feb; 117(2):291-5. doi: . [PMID: 14975218]
  • I N G Springer, H Terheyden, M A A Suhr, P Warnke, A Dunsche, M Tiemann, Y Açil. Follow-up of collagen crosslink excretion in patients with oral squamous cell carcinoma and analysis of tissue samples. British journal of cancer. 2003 Nov; 89(9):1722-8. doi: 10.1038/sj.bjc.6601325. [PMID: 14583776]
  • Ivo Barić, Kresimir Baraka, Miljenka Maradin, Dorotea Bartonicek, Vladimir Sarnavka, Davor Begović, Ksenija Fumić. [Glutaric aciduria type 1: an example of the importance of early detection of so-called cerebral organic aciduria]. Lijecnicki vjesnik. 2003 Nov; 125(11-12):312-6. doi: . [PMID: 15209027]
  • Kenneth M Towe. Evolution of protein amino acids. Science (New York, N.Y.). 2003 May; 300(5624):1370-1. doi: 10.1126/science.300.5624.1370d. [PMID: 12775820]
  • I N G Springer, H Terheyden, A Dunsche, N Czech, M A A Suhr, M Tiemann, J Hedderich, Y Açil. Collagen crosslink excretion and staging of oral cancer. British journal of cancer. 2003 Apr; 88(7):1105-10. doi: 10.1038/sj.bjc.6600873. [PMID: 12671712]
  • Frank Rauch, Mareile Georg, Angelika Stabrey, Christina Neu, Werner F Blum, Thomas Remer, Friedrich Manz, Eckhard Schoenau. Collagen markers deoxypyridinoline and hydroxylysine glycosides: pediatric reference data and use for growth prediction in growth hormone-deficient children. Clinical chemistry. 2002 Feb; 48(2):315-22. doi: . [PMID: 11805013]
  • R Swaminathan. Biochemical markers of bone turnover. Clinica chimica acta; international journal of clinical chemistry. 2001 Nov; 313(1-2):95-105. doi: 10.1016/s0009-8981(01)00656-8. [PMID: 11694245]
  • S Ono, N Shimizu, T Imai, G P Rodriguez. Urinary collagen metabolite excretion in amyotrophic lateral sclerosis. Muscle & nerve. 2001 Jun; 24(6):821-5. doi: 10.1002/mus.1075. [PMID: 11360267]
  • S Niiyama, S Koelker, I Degen, G F Hoffmann, R Happle, R Hoffmann. Acrodermatitis acidemica secondary to malnutrition in glutaric aciduria type I. European journal of dermatology : EJD. 2001 May; 11(3):244-6. doi: NULL. [PMID: 11358733]
  • J Zywiec, W Grzeszczak, K Pierzchała. [Bone complication in diabetes subjects with good metabolic control and without longterm complications: certain problems. Part II. Basal parameters of bone turnover]. Przeglad lekarski. 2001; 58(6):495-7. doi: . [PMID: 11816739]
  • J Zywiec, W Grzeszczak, K Pierzchała. [Bone complications in diabetic subjects with good metabolic control and without any long-term complications--certain problems. Part III: The influence of hypertension and type 2 diabetes mellitus co-incidence of calcium, phosphorus and magnesium metabolism]. Przeglad lekarski. 2001; 58(7-8):778-81. doi: NULL. [PMID: 11769386]
  • M Plebani, D Bernardi, M F Meneghetti, F Ujka, M Zaninotto. Biological variability in assessing the clinical value of biochemical markers of bone turnover. Clinica chimica acta; international journal of clinical chemistry. 2000 Sep; 299(1-2):77-86. doi: 10.1016/s0009-8981(00)00285-0. [PMID: 10900294]
  • B Casetta, M Romanello, L Moro. A rapid and simple method for quantitation of urinary hydroxylysyl glycosides, indicators of collagen turnover, using liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2000; 14(23):2238-41. doi: 10.1002/1097-0231(20001215)14:23<2238::aid-rcm157>3.0.co;2-a. [PMID: 11114034]
  • M J Seibel. Molecular markers of bone turnover: biochemical, technical and analytical aspects. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA. 2000; 11 Suppl 6(?):S18-29. doi: 10.1007/s001980070003. [PMID: 11193236]
  • V Lo Cascio, F Bertoldo, G Gambaro, E Gasperi, F Furlan, F Colapietro, C Lo Cascio, M Campagnola. Urinary galactosyl-hydroxylysine in postmenopausal osteoporotic women: A potential marker of bone fragility. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research. 1999 Aug; 14(8):1420-4. doi: 10.1359/jbmr.1999.14.8.1420. [PMID: 10457275]
  • D Euli, L Colombo, A Bruno, E Mussini. Assay for 5-hydroxylysine and L-lysine in human and rat urine and in bone by gas chromatography. Journal of chromatography. B, Biomedical sciences and applications. 1999 Mar; 724(2):373-9. doi: 10.1016/s0378-4347(98)00539-8. [PMID: 10219680]
  • B Morin, W A Bubb, M J Davies, R T Dean, S Fu. 3-Hydroxylysine, a potential marker for studying radical-induced protein oxidation. Chemical research in toxicology. 1998 Nov; 11(11):1265-73. doi: 10.1021/tx980118h. [PMID: 9815186]
  • S D Leigh, H S Ju, R Lundgard, G Y Daniloff, V Liu. Development of an immunoassay for urinary galactosylhydroxylysine. Journal of immunological methods. 1998 Nov; 220(1-2):169-78. doi: 10.1016/s0022-1759(98)00159-8. [PMID: 9839938]
  • A Jarisch, C Giunta, S Zielen, R König, B Steinmann. Sibs affected with both Ehlers-Danlos syndrome type IV and cystic fibrosis. American journal of medical genetics. 1998 Aug; 78(5):455-60. doi: 10.1002/(sici)1096-8628(19980806)78:5<455::aid-ajmg11>3.0.co;2-e. [PMID: 9714013]
  • M Zaninotto, D Bernardi, F Ujka, P Bonato, M Plebani. A proposal for standardizing urine collections for bone resorption markers measurement. Journal of clinical laboratory analysis. 1998; 12(3):145-9. doi: 10.1002/(sici)1098-2825(1998)12:3<145::aid-jcla3>3.0.co;2-8. [PMID: 9591700]
  • P Sirtori, C Sosio, R M Polo, R Tenni, A Rubinacci. A comparative study on biochemical markers of bone collagen breakdown in post-menopausal women. Pharmacological research. 1997 Sep; 36(3):229-35. doi: 10.1006/phrs.1997.0220. [PMID: 9367668]
  • P Collet, D Uebelhart, L Vico, L Moro, D Hartmann, M Roth, C Alexandre. Effects of 1- and 6-month spaceflight on bone mass and biochemistry in two humans. Bone. 1997 Jun; 20(6):547-51. doi: 10.1016/s8756-3282(97)00052-5. [PMID: 9177869]
  • M Pasquali, M J Still, T Vales, R I Rosen, J D Evinger, P P Dembure, N Longo, L J Elsas. Abnormal formation of collagen cross-links in skin fibroblasts cultured from patients with Ehlers-Danlos syndrome type VI. Proceedings of the Association of American Physicians. 1997 Jan; 109(1):33-41. doi: . [PMID: 9010914]
  • E Casari, M Alfano, M Valente, G D Clarke, G Ferni, B Grazioli. Ovariectomy in the rat induces a rapid increase in the urinary excretion of hydroxylysine glycosides and non-reducible crosslink residues. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA. 1997; 7(6):539-43. doi: 10.1007/bf02652559. [PMID: 9604049]
  • G Jonderko, E J Kucharz, M Fink, B Filipek, E Kotrys-Puchalska, A Wedrychowska. [Effect of heart infarction on levels of type I procollagen carboxyterminal peptide in blood serum]. Polskie Archiwum Medycyny Wewnetrznej. 1996 Dec; 96(6):528-35. doi: . [PMID: 9139272]
  • A Rubinacci, P Divieti, R M Polo, M Zampino, G Resmini, R Tenni. Effect of an oral calcium load on urinary markers of collagen breakdown. Journal of endocrinological investigation. 1996 Dec; 19(11):719-26. doi: 10.1007/bf03347874. [PMID: 9061504]
  • C Y Guo, W E Thomas, A W al-Dehaimi, A M Assiri, R Eastell. Longitudinal changes in bone mineral density and bone turnover in postmenopausal women with primary hyperparathyroidism. The Journal of clinical endocrinology and metabolism. 1996 Oct; 81(10):3487-91. doi: 10.1210/jcem.81.10.8855790. [PMID: 8855790]
  • A Pecile, C Netti, V Sibilia, I Villa, G Calori, R Tenni, M Coluzzi, G L Moro, A Rubinacci. Comparison between urinary pyridinium cross-links and hydroxylysine glycosides in monitoring the effects of ovariectomy and 17 beta-estradiol replacement in aged rats. The Journal of endocrinology. 1996 Sep; 150(3):383-90. doi: 10.1677/joe.0.1500383. [PMID: 8882157]
  • V Grazioli, M Alfano, A Stenico, E Casari. Urinary output of hydroxylysine glycosides and pyridinium cross-links in detecting rat bone collagen turnover rate. FEBS letters. 1996 Jun; 388(2-3):134-8. doi: 10.1016/0014-5793(96)00505-4. [PMID: 8690072]
  • R Marabini, P Sirtori, R Chionna, L Barzizza, A Rubinacci. Galactosylhydroxylysine and pyridinium cross links in monitoring the bone response to hormone replacement therapy. Journal of endocrinological investigation. 1996 Mar; 19(3):154-8. doi: 10.1007/bf03349858. [PMID: 8743280]
  • P Bettica, A K Taylor, J Talbot, L Moro, R Talamini, D J Baylink. Clinical performances of galactosyl hydroxylysine, pyridinoline, and deoxypyridinoline in postmenopausal osteoporosis. The Journal of clinical endocrinology and metabolism. 1996 Feb; 81(2):542-6. doi: 10.1210/jcem.81.2.8636265. [PMID: 8636265]
  • M Romanello, K Noris Suarez, P Bettica, L Moro. Detection of pyridinium cross-links in human bile. Calcified tissue international. 1995 Dec; 57(6):415-8. doi: 10.1007/bf00301942. [PMID: 8581871]
  • F Rauch, D Schnabel, M J Seibel, T Remer, A Stabrey, D Michalk, E Schönau. Urinary excretion of galactosyl-hydroxylysine is a marker of growth in children. The Journal of clinical endocrinology and metabolism. 1995 Apr; 80(4):1295-300. doi: 10.1210/jcem.80.4.7714103. [PMID: 7714103]
  • M Michalsky, J J Stepan, H Wilczek, J Formankova, L Moro. Galactosyl hydroxylysine in assessment of Paget's bone disease. Clinica chimica acta; international journal of clinical chemistry. 1995 Jan; 234(1-2):101-8. doi: 10.1016/0009-8981(94)05981-w. [PMID: 7758208]
  • H A Wollmann, E Schönau, W F Blum, F Meyer, K Kruse, M B Ranke. Dose-dependent responses in insulin-like growth factors, insulin-like growth factor-binding protein-3 and parameters of bone metabolism to growth hormone therapy in young adults with growth hormone deficiency. Hormone research. 1995; 43(6):249-56. doi: 10.1159/000184302. [PMID: 7541769]
  • M Alfano, E Casari, A Stenico, M Murone, V Grazioli. Improved HPLC determination of urinary hydroxylysine glycosides to study turnover rate of bone in humans and rats. Clinical chemistry. 1994 Nov; 40(11 Pt 1):2113-4. doi: 10.1093/clinchem/40.11.2113. [PMID: 7955391]
  • E J Kucharz. Serum hydroxyproline and hydroxylysine levels in patients with decompensated cirrhosis. Romanian journal of internal medicine = Revue roumaine de medecine interne. 1994 Oct; 32(4):271-4. doi: . [PMID: 7613499]
  • A K Taylor, S A Lueken, C Libanati, D J Baylink. Biochemical markers of bone turnover for the clinical assessment of bone metabolism. Rheumatic diseases clinics of North America. 1994 Aug; 20(3):589-607. doi: 10.1016/s0889-857x(21)00351-3. [PMID: 7984780]
  • V LoCascio, V Braga, F Bertoldo, P Bettica, A F Pasini, L Stefani, L Moro. Effect of bisphosphonate therapy and parathyroidectomy on the urinary excretion of galactosylhydroxylysine in primary hyperparathyroidism. Clinical endocrinology. 1994 Jul; 41(1):47-51. doi: 10.1111/j.1365-2265.1994.tb03783.x. [PMID: 8050131]
  • K Yoshihara, N Mochidome, T Hara, S Osada, A Takayama, M Nagata. Urinary excretion levels of hydroxylysine glycosides in osteoporotic patients. Biological & pharmaceutical bulletin. 1994 Jun; 17(6):836-9. doi: 10.1248/bpb.17.836. [PMID: 7951149]
  • G P Rodriguez, S L Garber. Prospective study of pressure ulcer risk in spinal cord injury patients. Paraplegia. 1994 Mar; 32(3):150-8. doi: 10.1038/sc.1994.28. [PMID: 8008417]
  • A Misiewicz, B Jeleń, K Radwan. [Excretion of hydroxylysine in urine of workers occupationally exposed to manganese]. Medycyna pracy. 1994; 45(4):319-23. doi: NULL. [PMID: 7968500]
  • P Bettica, D J Baylink, L Moro. Galactosyl hydroxylysine and deoxypyridinoline: a methodological comparison. European journal of clinical chemistry and clinical biochemistry : journal of the Forum of European Clinical Chemistry Societies. 1993 Jul; 31(7):459-65. doi: 10.1515/cclm.1993.31.7.459. [PMID: 8399787]
  • K Yoshihara, N Mochidome, Y Shida, Y Hayakawa, M Nagata. Pre-column derivatization and its optimum conditions for quantitative determination of urinary hydroxylysine glycosides by high-performance liquid chromatography. Biological & pharmaceutical bulletin. 1993 Jun; 16(6):604-7. doi: 10.1248/bpb.16.604. [PMID: 8364515]
  • V Grazioli, E Casari, M Murone, P A Bonini. High-performance liquid chromatographic method for measuring hydroxylysine glycosides and their ratio in urine as a possible marker of human bone collagen breakdown. Journal of chromatography. 1993 May; 615(1):59-66. doi: 10.1016/0378-4347(93)80290-k. [PMID: 8340463]
  • E Szołtysik, E J Kucharz. Serum markers of collagen metabolism in patients with diseases of the respiratory system. Romanian journal of internal medicine = Revue roumaine de medecine interne. 1993 Apr; 31(2):119-22. doi: NULL. [PMID: 8268829]
  • L Moro, K Noris-Suarez, M Michalsky, M Romanello, B de Bernard. The glycosides of hydroxylysine are final products of collagen degradation in humans. Biochimica et biophysica acta. 1993 Mar; 1156(3):288-90. doi: 10.1016/0304-4165(93)90044-9. [PMID: 8461318]
  • L Moro, C Gazzarrini, D Crivellari, E Galligioni, R Talamini, B de Bernard. Biochemical markers for detecting bone metastases in patients with breast cancer. Clinical chemistry. 1993 Jan; 39(1):131-4. doi: 10.1093/clinchem/39.1.131. [PMID: 8419037]
  • P Bettica, L Moro, S P Robins, A K Taylor, J Talbot, F R Singer, D J Baylink. Bone-resorption markers galactosyl hydroxylysine, pyridinium crosslinks, and hydroxyproline compared. Clinical chemistry. 1992 Nov; 38(11):2313-8. doi: . [PMID: 1424129]
  • E Schönau, K Kruse, B de Bernard, L Moro. Further evidence of elevated bone resorption in Ullrich-Turner syndrome by measuring urinary galactosyl-hydroxylysine. Acta paediatrica (Oslo, Norway : 1992). 1992 Aug; 81(8):633-4. doi: 10.1111/j.1651-2227.1992.tb12318.x. [PMID: 1392392]
  • G P Rodriquez, J Claus-Walker, G Reed. A study of osteoporosis as it relates to metabolic manifestations in edentulous women. The Journal of oral implantology. 1992; 18(4):379-82. doi: NULL. [PMID: 1298822]
  • J Mykała-Cieśla, J Gmiśki, M Machalski, M Drózdz. Evaluation of metabolism of connective tissue proteins in patients with lung cancer. Acta biochimica Polonica. 1992; 39(1):33-8. doi: NULL. [PMID: 1441832]
  • J A Dunn, D R McCance, S R Thorpe, T J Lyons, J W Baynes. Age-dependent accumulation of N epsilon-(carboxymethyl)lysine and N epsilon-(carboxymethyl)hydroxylysine in human skin collagen. Biochemistry. 1991 Feb; 30(5):1205-10. doi: 10.1021/bi00219a007. [PMID: 1899338]
  • P N Reddy, G D Raj, S C Dhar. Toxicological effects of an organophosphorus pesticide (dimethoate) on urinary collagen metabolites in normal and high protein diets fed female albino rats. Life sciences. 1991; 49(18):1309-18. doi: 10.1016/0024-3205(91)90195-h. [PMID: 1921647]
  • L J Beardsworth, D R Eyre, I R Dickson. Changes with age in the urinary excretion of lysyl- and hydroxylysylpyridinoline, two new markers of bone collagen turnover. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research. 1990 Jul; 5(7):671-6. doi: 10.1002/jbmr.5650050702. [PMID: 2118710]
  • L Dorland, M Duran, P K de Bree, G R Smith, A Horvath, A S Tibosch, S K Wadman. O-phosphohydroxylysinuria: a new inborn error of metabolism?. Clinica chimica acta; international journal of clinical chemistry. 1990 May; 188(3):221-6. doi: 10.1016/0009-8981(90)90203-5. [PMID: 2387074]
  • L Moro, C Gazzarrini, C Modricky, L Rovis, B de Bernard, E Galligioni, D Crivellari, S Morassut, S Monfardini. High predictivity of galactosyl-hydroxylysine in urine as an indicator of bone metastases from breast cancer. Clinical chemistry. 1990 May; 36(5):772-4. doi: 10.1093/clinchem/36.5.772. [PMID: 2337988]
  • D Uebelhart, E Gineyts, M C Chapuy, P D Delmas. Urinary excretion of pyridinium crosslinks: a new marker of bone resorption in metabolic bone disease. Bone and mineral. 1990 Jan; 8(1):87-96. doi: 10.1016/0169-6009(91)90143-n. [PMID: 2106358]
  • S Yamada, Y Aoto, T Suou, C Hirayama. Urinary hydroxyproline and hydroxylysine excretions in relation to hepatic hydroxyproline content in chronic liver disease. Clinical biochemistry. 1989 Oct; 22(5):389-93. doi: 10.1016/s0009-9120(89)80038-4. [PMID: 2805342]
  • J N Evans, D R Hemenway, J Kelley. Early markers of lung injury. Research report (Health Effects Institute). 1989 Sep; ?(29):1-17. doi: . [PMID: 2557865]
  • G P Rodriguez, J Claus-Walker, M C Kent, H M Garza. Collagen metabolite excretion as a predictor of bone- and skin-related complications in spinal cord injury. Archives of physical medicine and rehabilitation. 1989 Jun; 70(6):442-4. doi: 10.1016/0003-9993(89)90003-8. [PMID: 2730306]
  • L Moro, C Battista, C Modricky, L Rovis, B De Bernard, P Traldi, G Lubrano, F Marotti. High-performance liquid chromatographic preparation of galactosyl-hydroxylysine, a specific bone collagen marker. Journal of chromatography. 1989 May; 490(2):285-92. doi: 10.1016/s0378-4347(00)82786-3. [PMID: 2768402]
  • W Kulik, W Heerma, L Dorland, P K de Bree, M Duran. Fast-atom bombardment tandem mass spectrometry of phosphohydroxylysine and related phosphohydroxy amino acids. Rapid communications in mass spectrometry : RCM. 1989 Mar; 3(3):76-8. doi: 10.1002/rcm.1290030307. [PMID: 2520228]
  • T Ammitzbøll, S S Pedersen, F Espersen, H Schiøler. Excretion of urinary collagen metabolites correlates to severity of pulmonary disease in cystic fibrosis. Acta paediatrica Scandinavica. 1988 Nov; 77(6):842-6. doi: 10.1111/j.1651-2227.1988.tb10766.x. [PMID: 3144825]