FComEx: L-Homoserine (PC000082)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:04 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000082

FoodDB Record

FDB000522

Chemical Information

Name

L-Homoserine

Description

Present in germinating peas, Jack bean seeds (Canavalia ensiformis) and the seedlings of many leguminous plants Homoserine is a more reactive variant of the amino acid serine. In this variant, the hydroxyl side chain contains an additional CH2 group which brings the hydroxyl group closer to its own carboxyl group, allowing it to chemically react to form a five-membered ring. This occurs at the point that amino acids normally join to their neighbours in a peptide bond.; Homoserine is therefore unsuitable for forming proteins and has been eliminated from the repertoire of amino acids used by living things.; Homoserine is the final product on the C-terminal end of the N-terminal fragment following a cyanogen bromide cleavage. (wikipedia); Homoserine is an intermediate in the biosynthesis of three essential amino acids: methionine, threonine (an isomer of homoserine), and isoleucine. It forms by two reductions of aspartic acid via the intermediacy of aspartate semialdehyde.; Homoserine is an ?-amino acid with the chemical formula HO2CCH(NH2)CH2CH2OH. L-Homoserine is not one of the common amino acids encoded by DNA. It differs from the proteinogenic amino acid serine by insertion of an additional methylene group. Homoserine, or its lactone form, is the product of a cyanogen bromide cleavage of a peptide by degradation of methionine. L-Homoserine is found in many foods, some of which are cornmint, star fruit, common wheat, and nance.

CAS Number

672-15-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S)-2-amino-4-Hydroxybutanoate	Generator
(2S)-2-amino-4-hydroxybutanoic acid	biospider
(S)-2-amino-4-hydroxy-Butanoate	biospider
(S)-2-amino-4-hydroxy-Butanoic acid	biospider
(S)-2-Amino-4-hydroxybutanoate	biospider
(S)-2-Amino-4-hydroxybutanoic acid	biospider
(S)-2-Amino-4-hydroxybutyric acid	biospider
(s)-homoserine	biospider
2-amino-4-hydroxy-Butyrate	biospider
2-amino-4-hydroxy-Butyric acid	biospider
2-amino-4-hydroxy-L-Butyrate	biospider
2-amino-4-hydroxy-L-Butyric acid	biospider
2-Amino-4-hydroxybutanoate	biospider
2-Amino-4-hydroxybutanoic acid	biospider
2-Amino-4-hydroxybutanoic acid; L-form	db_source
2-Amino-4-hydroxybutyrate	biospider
2-Amino-4-hydroxybutyric acid	biospider
Butanoic acid, 2-amino-4-hydroxy-, (S)-	biospider
Butyric acid, 2-amino-4-hydroxy-, L-	biospider
Butyric acid, 2-amino-4-hydroxy-, L- (8CI)	biospider
Homoserine	biospider
Homoserine (van)	biospider
HSE	biospider
L-homoserine	biospider

Chemical Formula

C4H9NO3

IUPAC name

2-amino-4-hydroxybutanoic acid

InChI Identifier

InChI=1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)

InChI Key

UKAUYVFTDYCKQA-UHFFFAOYSA-N

Isomeric SMILES

NC(CCO)C(O)=O

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents