56224
L-(+)-Gulose
≥98.0% (HPLC)
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About This Item
Empirical Formula (Hill Notation):
C6H12O6
CAS Number:
Molecular Weight:
180.16
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352201
EC Number:
227-897-3
MDL number:
InChI key
WQZGKKKJIJFFOK-QRXFDPRISA-N
InChI
1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3+,4-,5-,6?/m0/s1
SMILES string
OC[C@@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
assay
≥98.0% (HPLC)
optical activity
[α]/D +23.0±2°, 24 hr, c = 0.5% in H2O
storage temp.
room temp
Application
L-(+)-Gulose, a rare aldohexose sugar C-3 epimer of galactose, is used in the development of various drugs and to glycosylate alginates. L-(+)-Gulose is a substrate of GDP-mannose 3′,5′-epimerase in plants and may be a precursor of L-ascorbic acid in plants.
Other Notes
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Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
Regulatory Information
涉药品监管产品
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Daniele Castagnolo et al.
Carbohydrate research, 344(11), 1285-1288 (2009-06-09)
An efficient and stereoselective synthesis of D,L-gulose was described. The key step of the synthetic route is represented by a multicomponent enyne cross metathesis-hetero Diels-Alder reaction which allows the formation of the pyran ring from cheap and commercially available substrates
Jasper Dinkelaar et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(30), 9400-9411 (2008-09-05)
The glycosylation properties of gulopyranosides have been mapped out, and it is shown that gulose has an intrinsic preference for the formation of 1,2-cis-glycosidic bonds. It is postulated that this glycosylation behaviour originates from nucleophilic attack at the oxacarbenium ion
Teruhide Sugisawa et al.
Bioscience, biotechnology, and biochemistry, 69(3), 659-662 (2005-03-24)
Ketogulonicigenium vulgare DSM 4025, known as a 2-keto-L-gulonic acid producing strain from L-sorbose via L-sorbosone, surprisingly produced L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone as the substrate under a growing or resting condition. As the best result, K. vulgare
Osamu Tamura et al.
Organic & biomolecular chemistry, 9(21), 7411-7419 (2011-09-08)
Stereoselective vinylogous Mannich reaction of 2-trimethylsilyloxyfuran with L-gulose-derived chiral nitrones in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate was investigated. The selectivity was strongly influenced by the bulkiness of the C-substituent of the nitrone: for example, C-benzyloxymethyl nitrone
G E Driver et al.
Carbohydrate research, 334(2), 81-89 (2001-08-15)
Displacement of the tosyloxy group in 5-O-benzyl-1,2-O-isopropylidene-4-O-(p-toluenesulfonyl)-alpha-D-glucoseptanose has yielded derivatives of 1,2-O-isopropylidene-alpha-D-galactoseptanose. Acid catalysed acetonation then gave 1,2:3,4-di-O-isopropylidene-alpha-D-galactoseptanose or 1,2;4,5-di-O-isopropylidene-alpha-D-galactoseptanose using lower acid concentrations. Reduction of the ketone derived from 1,2:3,4-O-isopropylidene-alpha-D-septanose gave 1,2;3,4-di-O-isopropylidene-beta-L-altroseptanose. Reaction of 3,4-anhydro-5-O-benzyl-1,2-O-isopropylidene-alpha-D-galactoseptanose with sodium methoxide gave
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