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UDP-glucosamine, also known as uridine diphosphate N-acetylglucosamine, is a crucial biomolecule involved in the biosynthesis of various complex carbohydrates and glycoconjugates. It is formed through the enzymatic reaction of N-acetylglucosamine-1-phosphate and UDP, catalyzed by the enzyme UDP-N-acetylglucosamine pyrophosphorylase. UDP-glucosamine serves as a donor of N-acetylglucosamine in the synthesis of peptidoglycan, a major component of bacterial cell walls, and plays a significant role in the formation of glycoproteins and glycolipids. This molecule is essential for maintaining cellular integrity and function, as well as for the proper functioning of the immune system.

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  • 17479-04-8 Structure
  • Basic information

    1. Product Name: UDP-glucosamine
    2. Synonyms: UDP-glucosamine
    3. CAS NO:17479-04-8
    4. Molecular Formula: C15H25N3O16P2
    5. Molecular Weight: 565.317022
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 17479-04-8.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: °Cat760mmHg
    3. Flash Point: °C
    4. Appearance: /
    5. Density: 1.93g/cm3
    6. Refractive Index: 1.671
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: UDP-glucosamine(CAS DataBase Reference)
    10. NIST Chemistry Reference: UDP-glucosamine(17479-04-8)
    11. EPA Substance Registry System: UDP-glucosamine(17479-04-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 17479-04-8(Hazardous Substances Data)

17479-04-8 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 17479-04-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,4,7 and 9 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 17479-04:
(7*1)+(6*7)+(5*4)+(4*7)+(3*9)+(2*0)+(1*4)=128
128 % 10 = 8
So 17479-04-8 is a valid CAS Registry Number.
InChI:InChI=1/C15H25N3O16P2/c16-8-11(23)9(21)5(3-19)32-14(8)33-36(28,29)34-35(26,27)30-4-6-10(22)12(24)13(31-6)18-2-1-7(20)17-15(18)25/h1-2,5-6,8-14,19,21-24H,3-4,16H2,(H,26,27)(H,28,29)(H,17,20,25)/t5-,6-,8-,9-,10-,11-,12-,13-,14-/m1/s1

17479-04-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name uridine-triphosphate

1.2 Other means of identification

Product number -
Other names 5'-UTP

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

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:17479-04-8 SDS

17479-04-8Relevant articles and documents

Exploring the broad nucleotide triphosphate and sugar-1-phosphate specificity of thymidylyltransferase Cps23FL from: Streptococcus pneumonia serotype 23F

Chen, Zonggang,Gu, Guofeng,Jin, Guoxia,Li, Siqiang,Wang, Hong

, p. 30110 - 30114 (2020/09/07)

Glucose-1-phosphate thymidylyltransferase (Cps23FL) from Streptococcus pneumonia serotype 23F is the initial enzyme that catalyses the thymidylyl transfer reaction in prokaryotic deoxythymidine diphosphate-l-rhamnose (dTDP-Rha) biosynthetic pathway. In this study, the broad substrate specificity of Cps23FL towards six glucose-1-phosphates and nine nucleoside triphosphates as substrates was systematically explored, eventually providing access to nineteen sugar nucleotide analogs.

Chemoenzymatic Synthesis of Unnatural Nucleotide Sugars for Enzymatic Bioorthogonal Labeling

Wen, Liuqing,Gadi, Madhusudhan Reddy,Zheng, Yuan,Gibbons, Christopher,Kondengaden, Shukkoor Muhammed,Zhang, Jiabin,Wang, Peng George

, p. 7659 - 7666 (2018/07/21)

In recent years, the development of the enzymatic bioorthogonal labeling strategy has offered exciting possibilities in the probing of structure-defined glycan epitopes. This strategy takes advantage of relaxed donor specificity and strict acceptor specificity of glycosyltransferases to label target glycan epitopes with bioorthogonal reactive groups carried by unnatural nucleotide sugars in vitro. The subsequent covalent conjugation by bioorthogonal chemical reactions with either fluorescent or affinity tags allows further visualization, quantification, or enrichment of target glycan epitopes. However, the application and development of the enzymatic labeling strategy have been hindered due to the limited availability of unnatural nucleotide sugars. Herein, a platform that combines chemical synthesis and enzymatic synthesis for the facile preparation of unnatural nucleotide sugars modified with diverse bioorthogonal reactive groups is described. By this platform, a total of 25 UDP-GlcNAc and UDP-GalNAc derivatives, including the most well explored bioorthogonal functional groups, were successfully synthesized. Furthermore, the potential application of these compounds for use in enzymatic bioorthogonal labeling reactions was also evaluated.

Compositions and methods for the transfer of a hexosamine to a modified nucleotide in a nucleic acid

-

, (2015/12/18)

Nucleic acids comprising β-glucosaminyloxy-5-methylcytosine; compositions, kits and methods of producing the nucleic acids using a glycosyltransferase; and methods of using the nucleic acids are described.

Enzymatic synthesis of nucleobase-modified UDP-sugars: Scope and limitations

Wagstaff, Ben A.,Rejzek, Martin,Pesnot, Thomas,Tedaldi, Lauren M.,Caputi, Lorenzo,O'Neill, Ellis C.,Benini, Stefano,Wagner, Gerd K.,Field, Robert A.

, p. 17 - 25 (2015/03/05)

Glucose-1-phosphate uridylyltransferase in conjunction with UDP-glucose pyrophosphorylase was found to catalyse the conversion of a range of 5-substituted UTP derivatives into the corresponding UDP-galactose derivatives in poor yield. Notably the 5-iodo derivative was not converted to UDP-sugar. In contrast, UDP-glucose pyrophosphorylase in conjunction with inorganic pyrophosphatase was particularly effective at converting 5-substituted UTP derivatives, including the iodo compound, into a range of gluco-configured 5-substituted UDP-sugar derivatives in good yields. Attempts to effect 4″-epimerization of these 5-substituted UDP-glucose with UDP-glucose 4″-epimerase from yeast were unsuccessful, while use of the corresponding enzyme from Erwinia amylovora resulted in efficient epimerization of only 5-iodo-UDP-Glc, but not the corresponding 5-aryl derivatives, to give 5-iodo-UDP-Gal. Given the established potential for Pd-mediated cross-coupling of 5-iodo-UDP-sugars, this provides convenient access to the galacto-configured 5-substituted-UDP-sugars from gluco-configured substrates and 5-iodo-UTP.

CHEMOENZYMATIC SYNTHESIS OF HEPARIN AND HEPARAN SULFATE ANALOGS

-

Paragraph 0304, (2014/09/03)

The present invention provides a one-pot multi-enzyme method for preparing UDP-sugars from simple sugar starting materials. The invention also provides a one-pot multi-enzyme method for preparing oligosaccharides from simple sugar starting materials.

Efficient one-pot multienzyme synthesis of UDP-sugars using a promiscuous UDP-sugar pyrophosphorylase from Bifidobacterium longum (BLUSP)

Muthana, Musleh M.,Qu, Jingyao,Li, Yanhong,Zhang, Lei,Yu, Hai,Ding, Li,Malekan, Hamed,Chen, Xi

supporting information; experimental part, p. 2728 - 2730 (2012/04/17)

A promiscuous UDP-sugar pyrophosphorylase (BLUSP) was cloned from Bifidobacterium longum strain ATCC55813 and used efficiently with a Pasteurella multocida inorganic pyrophosphatase (PmPpA) with or without a monosaccharide 1-kinase for one-pot multienzyme synthesis of UDP-galactose, UDP-glucose, UDP-mannose, and their derivatives. Further chemical diversification of a UDP-mannose derivative resulted in the formation of UDP-N-acetylmannosamine. The Royal Society of Chemistry 2012.

One-pot three-enzyme synthesis of UDP-GlcNAc derivatives

Chen, Yi,Thon, Vireak,Li, Yanhong,Yu, Hai,Ding, Li,Lau, Kam,Qu, Jingyao,Hie, Liana,Chen, Xi

, p. 10815 - 10817 (2011/11/04)

A Pasteurella multocida N-acetylglucosamine 1-phosphate uridylyltransferase (PmGlmU) was cloned and used efficiently with an N-acetylhexosamine 1-kinase (NahK-ATCC55813) and an inorganic pyrophosphatase (PmPpA) for one-pot three-enzyme synthesis of UDP-GlcNAc derivatives with or without further chemical diversification.

Exploiting nucleotidylyltransferases to prepare sugar nucleotides

Timmons, Shannon C.,Mosher, Roy H.,Knowles, Sheryl A.,Jakeman, David L.

, p. 857 - 860 (2007/10/03)

(Graph Presented) Enzymatic approaches to prepare sugar nucleotides are gaining in importance and offer several advantages over chemical synthesis including high yields and stereospecificity. We report the cloning, expression, and purification of two new wild-type thymidylyltransferases and observed catalysis with a wide variety of substrates. Significant product inhibition was not observed with the enzymes studied over a 24 h period, enabling the efficient preparation of 15 sugar nucleotides, clearly demonstrating the synthetic utility of these biocatalysts.

Chemoenzymatic synthesis of thio-nod factor intermediates - Enzymatic transfer of glucosamine on thiochitobiose derivatives

Morais, Latino Loureiro,Yuasa, Hideya,Bennis, Khalil,Ripoche, Isabelle,Auzanneau, France-Isabelle

, p. 587 - 596 (2007/10/03)

The chemoenzymatic syntheses of thioanalogues of nodulation factors in which the nonreducing end glucosamine residue is available for the introduction of the fatty acid moiety at the free NH2 group are reported. We are describing the chemical s

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