Classification Term: 531

Lipoamides (ontology term: CHEMONTID:0001154)

Compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring." []

found 4 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Dithiolanes

Child Taxonomies: There is no child term of current ontology term.

Lipoamide

5-(1,2-Dithiolan-3-yl)-pentanamide

C8H15NOS2 (205.05950199999998)


Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acids functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2). Lipoamide is the oxidized form of glutathione. (PMID:8957191) KEIO_ID L031; [MS2] KO009031 KEIO_ID L031

   

Lipoyllysine

(2R)-2-Amino-6-{[5-(1,2-dithiolan-3-yl)-1-hydroxypentylidene]amino}hexanoate

C14H26N2O3S2 (334.1384766)


lipollysine is an important lipoic acid derivative. Most alpha-lipoic acid in food is derived from lipoamide-containing enzymes and is bound to the amino acid, lysine (lipoyllysine). Animal tissues that are rich in lipoyllysine include kidney, heart, and liver, while plant sources that are rich in lipoyllysine include spinach, broccoli, and tomatoes. Somewhat lower amounts of lipoyllysine have been measured in peas, brussel sprouts, and rice bran. Lipoic acid can be found in many common foods such as potatoes, carrots, broccoli, yeasts, beets, yams, and red meat. Dietary sources of ALA include flaxseeds, flaxseed oil, canola (rapeseed) oil, soybeans and soybean oil, pumpkin seeds and pumpkin seed oil, purslane, perilla seed oil, walnuts and walnut oil. The best food sources of lipoic acid are believed to be those foods rich in mitochondria - red meat (skeletal muscle, heart, liver, kidney). Other sources are yeast, spinach, and broccoli. Lypoyllysine is involved in Lipoate metabolism pathway where lipoyllysine is undergo hydrolysis to produce liporate and l-lysine. lipollysine is an important lipoic acid derivative. Most alpha-lipoic acid in food is derived from lipoamide-containing enzymes and is bound to the amino acid, lysine (lipoyllysine). Animal tissues that are rich in lipoyllysine include kidney, heart, and liver, while plant sources that are rich in lipoyllysine include spinach, broccoli, and tomatoes. Somewhat lower amounts of lipoyllysine have been measured in peas, brussel sprouts, and rice bran. Lipoic acid can be found in many common foods such as potatoes, carrots, broccoli, yeasts, beets, yams, and red meat. Dietary sources of ALA include flaxseeds, flaxseed oil, canola (rapeseed) oil, soybeans and soybean oil, pumpkin seeds and pumpkin seed oil, purslane, perilla seed oil, walnuts and walnut oil. The best food sources of lipoic acid are believed to be those foods rich in mitochondria - red meat (skeletal muscle, heart, liver, kidney). Other sources are yeast, spinach, and broccoli.

   

N(6)-6(R,S)-lipoyl-L-lysine

2-Amino-6-[5-(1,2-dithiolane-3-yl)pentanoylamino]hexanoic acid

C14H26N2O3S2 (334.1384766)


   

Lysozyme

5-[(3R)-1,2-dithiolan-3-yl]pentanimidic acid

C8H15NOS2 (205.05950199999998)


Preservative. Prevents late blowing in semi-hard cheeses due to Clostridium tyrobutyricum. Lysozyme is part of the innate immune system. Children fed infant formula lack lysozyme in their diet and have three times the rate of diarrheal disease.[citation needed] Since lysozyme is a natural form of protection from pathogens like Salmonella, E.coli and Pseudomonas, when it is deficient due to infant formula feeding, can lead to increased incidence of disease.; Whereas the skin is a protective barrier due to its dryness and acidity, the conjunctiva (membrane covering the eye) is instead protected by secreted enzymes, mainly lysozyme and defensin. However, when these protective barriers fail, conjunctivitis results. Lysozyme is found in garden onion, papaya, and soft-necked garlic. Preservative. Prevents late blowing in semi-hard cheeses due to Clostridium tyrobutyricum