FComEx: L-Alloisoleucine (PC000200)

Record Information

Version

1.0

Creation date

2015-10-09 22:29:10 UTC

Update date

2017-01-19 02:36:16 UTC

FoodComEx ID

PC000200

FoodDB Record

FDB022117

Chemical Information

Name

L-Alloisoleucine

Description

L-alloisoleucine is a branched chain amino acid and is a stereo-isomer of L-isoleucine. It is a common constituent of human plasma (albeit at low levels). L-alloisoleucine is produced as a byproduct of isoleucine transamination. L-Isoleucine is one of the four common amino acids (the 3 others being threonine, hydroxyproline, and hydroxylysine) that have two asymmetric carbon atoms which produce four structural possibilities for the same chemical composition. L-alloisoleucine differs from L-isoleucine by having having different stereochemistry around its beta carbon. Plasma L-alloisoleucine, which is derived from L-isoleucine in vivo, can be used for the diagnosis of maple syrup urine disease (MSUD). Indeed, plasma L-alloisoleucine levels above 5 umol/L is the most specific and most sensitive diagnostic marker for all forms of MSUD (PMID: 10508118). In MSUD the degradation of the essential branched-chain L-amino acids leucine, valine, and isoleucine and their derived 2-oxoacids is impaired because of an inherited deficiency in branched-chain 2-oxoacid dehydrogenase complex (EC 1.2.4.4) activity. The accumulation of branched-chain compounds in blood and other body fluids can exert neurotoxic effects. [HMDB]

CAS Number

1509-34-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2S,3R)-2-amino-3-methylpentanoate	hmdb
(2S,3R)-2-amino-3-methylpentanoic acid	hmdb
(3R)-LS-Isoleucine	hmdb
[S-(R,S)]-2-Amino-3-methylpentanoate	hmdb
[S-(R,S)]-2-Amino-3-methylpentanoic acid	hmdb
2-amino-3-methyl-[S-(R,S)]-Pentanoate	hmdb
2-amino-3-methyl-[S-(R,S)]-Pentanoic acid	hmdb
Alle	ChEBI
Allo-Isoleucine	hmdb
Allo-L-Isoleucine	hmdb
L-allo-Isoleucine	hmdb
L-alloisoleucine	hmdb
L(+)-Alloisoleucine	hmdb
threo-3-methyl-L-Norvaline	hmdb
threo-L-Isoleucine	hmdb

Chemical Formula

C6H13NO2

IUPAC name

(2S,3R)-2-amino-3-methylpentanoic acid

InChI Identifier

InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5+/m1/s1

InChI Key

AGPKZVBTJJNPAG-UHNVWZDZSA-N

Isomeric SMILES

CC[C@@H](C)[C@H](N)C(O)=O

Average Molecular Weight

131.1729

Monoisotopic Molecular Weight

131.094628665

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Isoleucine and derivatives

Alternative Parents