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MetaCyc Compound: (R,R)-2,3-butanediol

Synonyms: D(-)-2,3-butanediol, 2,3-butylene glycol, 2,3-butanediol, butanediol, (R,R)-butane-2,3-diol, (R,R)-2,3-butylene glycol

Superclasses: an alcohola diola glycola 2,3-butanediol

2,3-butanediol is of commercial interest, mostly as an antifreeze agent due to to its low freezing point [Magee87]. One of its well known applications is the formation of methyl ethyl ketone, by dehydration, which can be used as a liquid fuel additive [Syu01]. All three stereo isomer of 2,3-butanediol ( (R,R)-2,3-butanediol, (S,S)-2,3-butanediol and (R,S)-2,3-butanediol) can be produced by various organisms [Wardwell01].

The metabolic function of 2,3-butanediol is not yet known, although it may play a role in preventing intracellular acidification by changing the metabolism from acid production to the formation of a neutral compound [Booth83]. In addition, the superpathway of (R,R)-butanediol biosynthesis pathway might participate in regulation of the NADH/NAD+ ratio. in the bacteria [Blomqvist93] .

Chemical Formula: C4H10O2

Molecular Weight: 90.122 Daltons

Monoisotopic Molecular Weight: 90.0680795652 Daltons

(R,R)-2,3-butanediol compound structure


InChI: InChI=1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4-/m1/s1


Unification Links: CAS:24347-58-8, ChEBI:16982, ChemSpider:196452, DrugBank:DB02418, HMDB:HMDB33007, KEGG:C03044, PubChem:225936

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 22.571203Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
a 6-phospho-β-D-galactoside + H2O → D-galactopyranose 6-phosphate + an alcohol
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol

Reactions known to both consume and produce the compound:

(R,R)-butanediol biosynthesis , (R,R)-butanediol degradation :
(R,R)-2,3-butanediol + NAD+ ↔ (R)-acetoin + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
an epoxide + H2O = a glycol

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
trans-cinnamoyl-β-D-glucoside + an alcohol = alkyl cinnamate + D-glucopyranose
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes inhibited by (R,R)-2,3-butanediol, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: 2,7,4-trihydroxyisoflavanone hydro-lyase (daidzein-forming) [Hakamatsuka98]

This compound has been characterized as an alternative substrate of the following enzymes: xylitol dehydrogenase, glycerol dehydrogenase, cyclic alcohol dehydrogenase


Blomqvist93: Blomqvist K, Nikkola M, Lehtovaara P, Suihko ML, Airaksinen U, Straby KB, Knowles JK, Penttila ME (1993). "Characterization of the genes of the 2,3-butanediol operons from Klebsiella terrigena and Enterobacter aerogenes." J Bacteriol 175(5);1392-404. PMID: 8444801

Booth83: Booth IR, Kroll RG (1983). "Regulation of cytoplasmic pH (pH1) in bacteria and its relationship to metabolism." Biochem Soc Trans 11(1);70-2. PMID: 6298028

Hakamatsuka98: Hakamatsuka T, Mori K, Ishida S, Ebizuka Y, Sankawa U (1998). "Purification of 2-hydroxyisoflavanone dehydratase from the cell cultures of Pueraria lobata." Phytochemistry 49(2);497-505.

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

Magee87: Magee, R.J., Kosaric, N. (1987). "The microbial production of 2,3-butanediol." Adv. Appl. Microbiol. 32: 89-161.

Syu01: Syu MJ (2001). "Biological production of 2,3-butanediol." Appl Microbiol Biotechnol 55(1);10-8. PMID: 11234948

Wardwell01: Wardwell SA, Yang YT, Chang HY, San KY, Rudolph FB, Bennett GN (2001). "Expression of the Klebsiella pneumoniae CG21 acetoin reductase gene in Clostridium acetobutylicum ATCC 824." J Ind Microbiol Biotechnol 27(4);220-7. PMID: 11687934

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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