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MetaCyc Compound: L-galactono-1,4-lactone

Synonyms: L-galactono-γ-lactone, L-galactonate-γ-lactone, L-galactonic acid-γ-lactone, L-galactonic acid-g-lactone

Superclasses: an ester a lactone a gamma-lactone

Chemical Formula: C6H10O6

Molecular Weight: 178.14 Daltons

Monoisotopic Molecular Weight: 178.0477380536 Daltons

L-galactono-1,4-lactone compound structure

SMILES: C(O)C(O)[CH]1(C(O)C(O)C(=O)O1)

InChI: InChI=1S/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2-,3-,4-,5+/m0/s1

InChIKey: InChIKey=SXZYCXMUPBBULW-NEEWWZBLSA-N

Unification Links: CAS:1668-08-2 , ChEBI:17464 , ChemSpider:388522 , KEGG:C01115 , PubChem:6857365

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -113.06881 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

L-ascorbate biosynthesis I (L-galactose pathway) :
L-galactono-1,4-lactone + 2 an oxidized c-type cytochrome → L-ascorbate + 2 a reduced c-type cytochrome + 3 H+

L-ascorbate biosynthesis V :
L-galactono-1,4-lactone + an oxidized unknown electron acceptor → L-ascorbate + an reduced unknown electron acceptor + H+

Not in pathways:
L-galactono-1,4-lactone + oxygen → L-ascorbate + hydrogen peroxide + H+

Reactions known to produce the compound:

L-ascorbate biosynthesis I (L-galactose pathway) :
L-galactopyranose + NAD+L-galactono-1,4-lactone + NADH + H+

Not in pathways:
L-galactono-1,5-lactone → L-galactono-1,4-lactone

Reactions known to both consume and produce the compound:

L-ascorbate biosynthesis V :
aldehydo-L-galactonate + H+L-galactono-1,4-lactone + H2O

In Reactions of unknown directionality:

Not in pathways:
L-galactono-1,4-lactone + 4 an oxidized c-type cytochrome = L-dehydro-ascorbate + 4 a reduced c-type cytochrome + 4 H+

Enzymes inhibited by L-galactono-1,4-lactone, sorted by the type of inhibition, are:

Inhibitor (Allosteric) of: GDP-D-mannose:GDP-L-gulose epimerase [Wolucka03] , GDP-D-mannose:GDP-L-gulose epimerase [Wolucka03]

Inhibitor (Mechanism unknown) of: GDP-D-mannose-3'',5''-epimerase [Wolucka03]

This compound has been characterized as an alternative substrate of the following enzymes: L-gulono-γ-lactone oxidase , L-galactono-1,5-lactonase , gluconolactonase


References

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

Wolucka03: Wolucka BA, Van Montagu M (2003). "GDP-mannose 3',5'-epimerase forms GDP-L-gulose, a putative intermediate for the de novo biosynthesis of vitamin C in plants." J Biol Chem 278(48);47483-90. PMID: 12954627


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 SRI International Pathway Tools version 19.0 on Tue Sep 1, 2015, biocyc11.