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18186-48-6

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  • [(2S,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[(2R,3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxo-oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-phosphinic acid

    Cas No: 18186-48-6

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  • (2S,3S,4R,5R)-5-(2-AMINO-6-OXO-3H-PURIN-9-YL)-3,4-DIHYDROXY-OXOLAN-2-YL]METHOXY-[[(2R,3R,4S,6S)-3,4-DIHYDROXY-6-METHYL-5-OXO-OXAN-2-YL]OXY-HYDROXY-PHOSPHORYL]OXY-PHOSPHINIC ACIDCAS

    Cas No: 18186-48-6

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18186-48-6 Usage

Definition

ChEBI: A GDP-sugar having 4-dehydro-6-deoxy-alpha-D-mannose as the sugar portion.

Check Digit Verification of cas no

The CAS Registry Mumber 18186-48-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,1,8 and 6 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 18186-48:
(7*1)+(6*8)+(5*1)+(4*8)+(3*6)+(2*4)+(1*8)=126
126 % 10 = 6
So 18186-48-6 is a valid CAS Registry Number.
InChI:InChI=1/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1

18186-48-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name GDP-4-dehydro-6-deoxy-α-D-mannose

1.2 Other means of identification

Product number -
Other names GDP-4-dehydro-6-deoxy-D-mannose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:18186-48-6 SDS

18186-48-6Relevant articles and documents

Mechanism and active site residues of GDP-fucose synthase

Lau, Stephen T. B.,Tanner, Martin E.

experimental part, p. 17593 - 17602 (2009/07/19)

L-Fucose, 6-deoxy-L-galactose, is a key component of many important glycoconjugates including the blood group antigens and the Lewisx ligands. The biosynthesis of GDP-L-fucose begins with the action cof a dehydratase that converts GDP-D-mannose into GDP-4-keto-6-deoxy-mannose. The enzyme GDP-fucose synthase, GFS, (also known as GDP-4-keto-6-deoxy-D-mannose epimerase/reductase, GMER) then converts GDP-4-keto-6-deoxy-D-mannose into GDP-L-fucose. The GFS reaction involves epimerizations at both C-3 and C-5 followed by an NADPH-dependent reduction of the carbonyl at C-4. This manuscript describes studies that elucidate the order of the epimerization steps and the roles of the active site acid/base residues responsible for the epimerizations. An active site mutant, Cys109Ser, produces GDP-6-deoxy-D-altrose as its major product indicating that C-3 epimerization occurs first and premature reduction of the GDP-4-keto-6-deoxy-D-altrose intermediate becomes competitive with GDP-L-fucose production. The same mutation results in the appearance of a kinetic isotope effect when [3 - 2H]-GDP-6-deoxy-4-keto- mannose is used as a substrate. This indicates that Cys109 is the base responsible for the deprotonation of the substrate at C-3. The Cys109Ser mutant also catalyzes a rapid wash-in of solvent derived deuterium into the C-5 position of GDP-fucose in the presence of NADP+. This confirms the order of epimerizations and the role of Cys109. Finally, the inactive His179Gln mutant readily catalyzes the wash-out of deuterium from the C-3 position of [3 - 2H]-GDP-6- deoxy-4-keto-mannose. Together these results strongly implicate an ordered sequence of epimerizations (C-3 followed by C-5 ) and suggest that Cys109 acts as a base and His179 acts as an acid in both epimerization steps.

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