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00338

Sigma-Aldrich

(3S)-3,4-Dihydroxy-2-butanone

≥95% (GC)

Synonym(s):

1-Deoxy-L-erythrulose

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About This Item

Empirical Formula (Hill Notation):
C4H8O3
CAS Number:
161972-10-7
Molecular Weight:
104.10
Beilstein/REAXYS Number:
8899170
MDL number:
MFCD28016583
UNSPSC Code:
12352201
PubChem Substance ID:
329747044

assay

≥95% (GC)

form

liquid

optical activity

[α]/D 78±4°, c = 1 in H2O

storage temp.

−20°C

SMILES string

OC[C@@H](C(C)=O)O

InChI

1S/C4H8O3/c1-3(6)4(7)2-5/h4-5,7H,2H2,1H3/t4-/m0/s1

InChI key

SEYLPRWNVFCVRQ-BYPYZUCNSA-N

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Stefanie Echt et al.
Journal of molecular biology, 341(4), 1085-1096 (2004-08-27)
A synthetic gene specifying a putative 3,4-dihydroxy-2-butanone 4-phosphate synthase of Candida albicans directed the synthesis of a 22.5 kDa peptide in a recombinant Escherichia coli strain. The recombinant protein was purified to apparent homogeneity by two chromatographic steps and was
K Ritsert et al.
Journal of molecular biology, 253(1), 151-167 (1995-10-13)
The lumazine synthase/riboflavin synthase of Bacillus subtilis is a bifunctional enzyme complex catalysing the formation of riboflavin from 5-amino-6-(D-ribitylamino)-2,4(1H,3H)-pyrimidinedione and L-3,4-dihydroxy-2-butanone-4-phosphate via 6,7-dimethyl-8-ribityllumazine. The complex is composed of 3 alpha (riboflavin synthase) subunits and 60 beta (lumazine synthase) subunits and
K Kis et al.
Biochemistry, 34(9), 2883-2892 (1995-03-07)
The lumazine synthase/riboflavin synthase complex of Bacillus subtilis consists of an icosahedral capsid of 60 beta subunits surrounding a core of 3 alpha subunits. The beta subunits catalyze the condensation of 5-amino-6-ribitylamino-2,4(1H,3H)-pyrimidinedione with (3S)-3,4-dihydroxy-2-butanone under formation of 6,7-dimethyl-8-ribityllumazine. This intermediate
Biosynthesis of riboflavin. The structure of the purine precursor.
A Bacher et al.
The Journal of biological chemistry, 248(17), 6227-6231 (1973-09-10)
Rudolf Ladenstein et al.
The FEBS journal, 280(11), 2537-2563 (2013-04-05)
The xylene ring of riboflavin (vitamin B2 ) is assembled from two molecules of 3,4-dihydroxy-2-butanone 4-phosphate by a mechanistically complex process that is jointly catalyzed by lumazine synthase and riboflavin synthase. In Bacillaceae, these enzymes form a structurally unique complex comprising

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