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MetaCyc Compound: (R)-lipoate

Systematic Name: 1,2-dithiolane-3-pentanoic acid

Synonyms: α-liponic acid, 5-(1,2-dithiolan-3-yl)-pentanoate, lipoic acid, 6,8-thioctic acid, 6,8-thioctate, DL-thioctic acid, DL-thioctate

Superclasses: a cofactora prosthetic group

Lipoate is an organosulfur compound that is used as an essential cofactor by many enzyme complexes. The functional group of lipoate is a ditholane ring, which is a cyclic disulfide.

The enzyme complexes that require lipoate have a dedicated lipoyl domain, and lipoate is actually produced on this domain. The precursor octanoate molecule is first attached to a specific L-lysine residue within the lipoyl domain, and is then converted to lipoate by the enzyme lipoyl synthase, which is also the source of the two sulfur atoms.

Lipoate can be dettached from the enzyme complex by a dedicated lipoamidase, and be re-attached to the complex by the enzyme lipoate protein ligase.

Chemical Formula: C8H13O2S2

Molecular Weight: 205.31 Daltons

Monoisotopic Molecular Weight: 206.0435210736 Daltons

(<i>R</i>)-lipoate compound structure


InChI: InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/p-1/t7-/m1/s1


Unification Links: CAS:62-46-4, ChEBI:83088, ChemSpider:841, HMDB:HMDB01451, KEGG:C16241, MetaboLights:MTBLC30313, PubChem:1549144

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 69.232506Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

lipoate salvage I , lipoate salvage II :
ATP + (R)-lipoate + H+ → lipoyl-adenylate + diphosphate

Not in pathways:
[glycine cleavage system lipoyl-carrier protein]-L-lysine + ATP + (R)-lipoate → AMP + a [glycine-cleavage complex H protein] N6-lipoyl-L-lysine + diphosphate + H+

Reactions known to produce the compound:

arsenate detoxification I (glutaredoxin) :
ribose-1-arsenate + dihydrolipoate + H+ → D-ribofuranose + arsenite + (R)-lipoate

lipoate salvage II :
a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + H2O → a [lipoyl-carrier protein]-L-lysine + (R)-lipoate

Reactions known to both consume and produce the compound:

Not in pathways:
5-aminopentanoate + (R)-lipoate ↔ dihydrolipoate + D-proline

In Reactions of unknown directionality:

Not in pathways:
a [lipoyl-carrier protein]-L-lysine + ATP + (R)-lipoate = a [lipoyl-carrier protein]-N6-lipoyl-L-lysine + AMP + diphosphate + H+

In Transport reactions:

Enzymes activated by (R)-lipoate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: glycine decarboxylase [Hiraga80]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: dihydrolipoyllysine-residue acetyltransferase, lipoamide acyltransferase

Revised 12-Nov-2009 by Caspi R, SRI International
Reviewed 03-Oct-2013 by Foerster H, Boyce Thompson Institute


Hiraga80: Hiraga K, Kikuchi G (1980). "The mitochondrial glycine cleavage system. Purification and properties of glycine decarboxylase from chicken liver mitochondria." J Biol Chem 255(24);11664-70. PMID: 7440562

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Mon May 2, 2016, biocyc14.