Maltotriose (BioDeep_00000001626)

 

Secondary id: BioDeep_00000001107, BioDeep_00000398075, BioDeep_00001868448

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


代谢物信息卡片


(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

化学式: C18H32O16 (504.1690272)
中文名称: 麦芽三糖
谱图信息: 最多检出来源 Homo sapiens(feces) 0.06%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Maltotriose. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/maltotriose (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000001626). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(OC(C(C3O)O)O)CO)CO)O)O)O)O
InChI: InChI=1/C18H32O16/c19-1-4-7(22)8(23)12(27)17(31-4)34-15-6(3-21)32-18(13(28)10(15)25)33-14-5(2-20)30-16(29)11(26)9(14)24/h4-29H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16?,17-,18-/m1/s1

描述信息

Maltotriose is a trisaccharide (three-part sugar) consisting of three glucose molecules linked with α-1,4 glycosidic bonds. It is most commonly produced by the digestive enzyme alpha-amylase (a common enzyme in human saliva) on amylose in starch. The creation of both maltotriose and maltose during this process is due to the random manner in which alpha amylase hydrolyses α-1,4 glycosidic bonds. It is the shortest chain oligosaccharide that can be classified as maltodextrin. Maltotriose belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Maltotriose is a common oligosaccharide metabolite found in human urine after maltose ingestion or infusion (PMID:6645121). Maltotriose is increased in glycogen storage disease II (OMIM: 232300) due to a mutation of the enzyme alpha-1,4-glucosidase (EC 3.2.1.20) (PMID:4286143).
Constituent of corn syrup. Amylolysis production from starch. Maltooligosaccharide mixtures are important food additives (sweeteners, gelling agents and viscosity modifiers)
Acquisition and generation of the data is financially supported in part by CREST/JST.
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Maltotriose, the second most abundant sugar present in brewing, is an inducer of the maltose regulon of Escherichia coli. Maltotriose can induce beta-galactosidase synthesis[1][2].
Maltotriose, the second most abundant sugar present in brewing, is an inducer of the maltose regulon of Escherichia coli. Maltotriose can induce beta-galactosidase synthesis[1][2].

同义名列表

20 个代谢物同义名

(2R,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol; O-alpha-delta-Glucopyranosyl-(1beta94)-O-alpha-delta-glucopyranosyl-(1beta94)-O-alpha-delta-glucose; O-alpha-D-Glucopyranosyl-(1beta94)-O-alpha-D-glucopyranosyl-(1beta94)-O-alpha-D-glucose; WURCS=2.0/2,3,2/[a2122h-1x_1-5][a2122h-1a_1-5]/1-2-2/a4-b1_b4-C1; alpha-D-Glucosyl-(1->4)-alpha-D-glucosyl-(1->4)-D-glucoose; a-D-Glucosyl-(1->4)-a-D-glucosyl-(1->4)-D-glucoose; Α-D-glucosyl-(1->4)-α-D-glucosyl-(1->4)-D-glucoose; alpha-D-GLC-(1->4)-alpha-D-GLC-(1->4)-D-GLC; 4-O-(4-O-Hexopyranosylhexopyranosyl)hexose; a-D-GLC-(1->4)-a-D-GLC-(1->4)-D-GLC; Α-D-GLC-(1->4)-α-D-GLC-(1->4)-D-GLC; Glcalpha1-4glcalpha1-4GLC; delta-(+)-Maltotriose; D-(+)-Cellotriose; D-(+)-Maltotriose; D-Maltotriose; Amylotriose; Maltotriose; Maltotriose; Maltotriose



数据库引用编号

38 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(1)

代谢反应

167 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(24)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(136)

COVID-19 Disease Map(1)

PathBank(6)

PharmGKB(0)

21 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

  • Eun Yeong Jang, Ki-Bae Hong, Yeok Boo Chang, Jungcheul Shin, Eun Young Jung, Kyungae Jo, Hyung Joo Suh. In Vitro Prebiotic Effects of Malto-Oligosaccharides Containing Water-Soluble Dietary Fiber. Molecules (Basel, Switzerland). 2020 Nov; 25(21):. doi: 10.3390/molecules25215201. [PMID: 33182247]
  • Virve Vidgren, Brian Gibson. Trans-regulation and localization of orthologous maltose transporters in the interspecies lager yeast hybrid. FEMS yeast research. 2018 09; 18(6):. doi: 10.1093/femsyr/foy065. [PMID: 29931058]
  • Nicolas Sauvageot, Abdelhamid Mokhtari, Philippe Joyet, Aurélie Budin-Verneuil, Víctor S Blancato, Guillermo D Repizo, Céline Henry, Andreas Pikis, John Thompson, Christian Magni, Axel Hartke, Josef Deutscher. Enterococcus faecalis Uses a Phosphotransferase System Permease and a Host Colonization-Related ABC Transporter for Maltodextrin Uptake. Journal of bacteriology. 2017 05; 199(9):. doi: 10.1128/jb.00878-16. [PMID: 28242718]
  • Jing Li, Wenxu Zhou, Perigio Francisco, Russell Wong, Dongke Zhang, Steven M Smith. Inhibition of Arabidopsis chloroplast β-amylase BAM3 by maltotriose suggests a mechanism for the control of transitory leaf starch mobilisation. PloS one. 2017; 12(2):e0172504. doi: 10.1371/journal.pone.0172504. [PMID: 28225829]
  • Yallappa Rajashekar, Thimmappa Shivanandappa. Mode of Action of the Natural Insecticide, Decaleside Involves Sodium Pump Inhibition. PloS one. 2017; 12(1):e0170836. doi: 10.1371/journal.pone.0170836. [PMID: 28125742]
  • Daniela Gutsch, Dietmar Appelhans, Sabrina Höbel, Brigitte Voit, Achim Aigner. Biocompatibility and efficacy of oligomaltose-grafted poly(ethylene imine)s (OM-PEIs) for in vivo gene delivery. Molecular pharmaceutics. 2013 Dec; 10(12):4666-75. doi: 10.1021/mp400479g. [PMID: 24175860]
  • Marina Camara Mattos Martins, Mahdi Hejazi, Joerg Fettke, Martin Steup, Regina Feil, Ursula Krause, Stéphanie Arrivault, Daniel Vosloh, Carlos María Figueroa, Alexander Ivakov, Umesh Prasad Yadav, Maria Piques, Daniela Metzner, Mark Stitt, John Edward Lunn. Feedback inhibition of starch degradation in Arabidopsis leaves mediated by trehalose 6-phosphate. Plant physiology. 2013 Nov; 163(3):1142-63. doi: 10.1104/pp.113.226787. [PMID: 24043444]
  • Lin Liu, Nicola L B Pohl. Synthesis of a series of maltotriose phosphates with an evaluation of the utility of a fluorous phosphate protecting group. Carbohydrate research. 2013 Mar; 369(?):14-24. doi: 10.1016/j.carres.2012.12.015. [PMID: 23376679]
  • Barbara Ziemba, Inessa Halets, Dzmitry Shcharbin, Dietmar Appelhans, Brigitte Voit, Ireneusz Pieszynski, Maria Bryszewska, Barbara Klajnert. Influence of fourth generation poly(propyleneimine) dendrimers on blood cells. Journal of biomedical materials research. Part A. 2012 Nov; 100(11):2870-80. doi: 10.1002/jbm.a.34222. [PMID: 22623362]
  • Joanna Drzewińska, Dietmar Appelhans, Brigitte Voit, Maria Bryszewska, Barbara Klajnert. Poly(propylene imine) dendrimers modified with maltose or maltotriose protect phosphorothioate oligodeoxynucleotides against nuclease activity. Biochemical and biophysical research communications. 2012 Oct; 427(1):197-201. doi: 10.1016/j.bbrc.2012.09.043. [PMID: 22995301]
  • Hidetaka Akita, Tomoya Masuda, Takashi Nishio, Kenichi Niikura, Kuniharu Ijiro, Hideyoshi Harashima. Improving in vivo hepatic transfection activity by controlling intracellular trafficking: the function of GALA and maltotriose. Molecular pharmaceutics. 2011 Aug; 8(4):1436-42. doi: 10.1021/mp200189s. [PMID: 21598999]
  • Jong-Hyun Kim, Michihiro Sunako, Hisayo Ono, Yoshikatsu Murooka, Eiichiro Fukusaki, Mitsuo Yamashita. Characterization of gene encoding amylopullulanase from plant-originated lactic acid bacterium, Lactobacillus plantarum L137. Journal of bioscience and bioengineering. 2008 Nov; 106(5):449-59. doi: 10.1263/jbb.106.449. [PMID: 19111640]
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  • Udo Schnupf, Julious L Willett, Wayne B Bosma, Frank A Momany. DFT conformational studies of alpha-maltotriose. Journal of computational chemistry. 2008 May; 29(7):1103-12. doi: 10.1002/jcc.20872. [PMID: 18069685]
  • Sergio L Alves, Ricardo A Herberts, Claudia Hollatz, Debora Trichez, Luiz C Miletti, Pedro S de Araujo, Boris U Stambuk. Molecular analysis of maltotriose active transport and fermentation by Saccharomyces cerevisiae reveals a determinant role for the AGT1 permease. Applied and environmental microbiology. 2008 Mar; 74(5):1494-501. doi: 10.1128/aem.02570-07. [PMID: 18203856]
  • Noriyuki Doukyu, Wataru Yamagishi, Hirokazu Kuwahara, Hiroyasu Ogino, Noritake Furuki. Purification and characterization of a maltooligosaccharide-forming amylase that improves product selectivity in water-miscible organic solvents, from dimethylsulfoxide-tolerant Brachybacterium sp. strain LB25. Extremophiles : life under extreme conditions. 2007 Nov; 11(6):781-8. doi: 10.1007/s00792-007-0096-8. [PMID: 17619813]
  • Chun Tang, Charles D Schwieters, G Marius Clore. Open-to-closed transition in apo maltose-binding protein observed by paramagnetic NMR. Nature. 2007 Oct; 449(7165):1078-82. doi: 10.1038/nature06232. [PMID: 17960247]
  • W Haas, C Wulff, K Grabe, V Meyer, S Haeberlein. Navigation within host tissues: cues for orientation of Diplostomum spathaceum (Trematoda) in fish towards veins, head and eye. Parasitology. 2007 Jul; 134(Pt 7):1013-23. doi: 10.1017/s0031182007002430. [PMID: 17316474]
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  • Nicole S Bresolin, Zhongyi Li, Behjat Kosar-Hashemi, Ian J Tetlow, Manash Chatterjee, Sadequr Rahman, Matthew K Morell, Crispin A Howitt. Characterisation of disproportionating enzyme from wheat endosperm. Planta. 2006 Jun; 224(1):20-31. doi: 10.1007/s00425-005-0187-7. [PMID: 16333636]
  • Birte Kramhøft, Kristian Sass Bak-Jensen, Haruhide Mori, Nathalie Juge, Jane Nøhr, Birte Svensson. Involvement of individual subsites and secondary substrate binding sites in multiple attack on amylose by barley alpha-amylase. Biochemistry. 2005 Feb; 44(6):1824-32. doi: 10.1021/bi048100v. [PMID: 15697208]
  • Angelo J B Dias, Marcos S Maia, Claudio A Retamal, María Luisa López. Identification and partial characterization of alpha-1,4-glucosidase activity in equine epididymal fluid. Theriogenology. 2004 May; 61(7-8):1545-58. doi: 10.1016/j.theriogenology.2003.09.004. [PMID: 15036984]
  • Michael M Palian, V I Boguslavsky, David F O'Brien, Robin Polt. Glycopeptide-membrane interactions: glycosyl enkephalin analogues adopt turn conformations by NMR and CD in amphipathic media. Journal of the American Chemical Society. 2003 May; 125(19):5823-31. doi: 10.1021/ja0268635. [PMID: 12733923]
  • Frank Orlik, Christian Andersen, Roland Benz. Site-directed mutagenesis of tyrosine 118 within the central constriction site of the LamB (maltoporin) channel of Escherichia coli. II. Effect on maltose and maltooligosaccharide binding kinetics. Biophysical journal. 2002 Jul; 83(1):309-21. doi: 10.1016/s0006-3495(02)75171-0. [PMID: 12080122]
  • Hee-Kyung Bae, Soo-Bok Lee, Cheon-Seok Park, Jae-Hoon Shim, Hye-Young Lee, Myo-Jeong Kim, Jin-Sook Baek, Hoe-Jin Roh, Jin-Hwan Choi, Eun-Ok Choe, Dong-Uk Ahn, Kwan-Hwa Park. Modification of ascorbic acid using transglycosylation activity of Bacillus stearothermophilus maltogenic amylase to enhance its oxidative stability. Journal of agricultural and food chemistry. 2002 May; 50(11):3309-16. doi: 10.1021/jf011550z. [PMID: 12010003]
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  • C Hollatz, B U Stambuk. Colorimetric determination of active alpha-glucoside transport in Saccharomyces cerevisiae. Journal of microbiological methods. 2001 Sep; 46(3):253-9. doi: 10.1016/s0167-7012(01)00281-0. [PMID: 11438190]
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