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Literature DB >> 11483049

Improved chemical synthesis of UDP-galactofuranose.

Abstract

[reaction: see text] A reliable and efficient synthetic route to UDP-alpha-D-galactofuranose (UDP-Galf) has been developed. Reaction of UMP-N-methylimidazolide with Galf 1-phosphate proceeds rapidly to provide UDP-Galf with excellent reproducibility and in a yield approximately twice as high as those reported previously.

Entities: Chemical

Mesh：

Substances：

Year: 2001 PMID： 11483049 DOI： 10.1021/ol016170d

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

15 in total

Review 1. Targeting the formation of the cell wall core of M. tuberculosis.

Authors: Clifton E Barry; Dean C Crick; Michael R McNeil
Journal: Infect Disord Drug Targets Date: 2007-06

2. Monitoring processivity and length control of a carbohydrate polymerase.

Authors: Matthew R Levengood; Rebecca A Splain; Laura L Kiessling
Journal: J Am Chem Soc Date: 2011-07-25 Impact factor: 15.419

3. Fluorosugar chain termination agents as probes of the sequence specificity of a carbohydrate polymerase.

Authors: Christopher D Brown; Max S Rusek; Laura L Kiessling
Journal: J Am Chem Soc Date: 2012-04-10 Impact factor: 15.419

4. Comparing Galactan Biosynthesis in Mycobacterium tuberculosis and Corynebacterium diphtheriae.

Authors: Darryl A Wesener; Matthew R Levengood; Laura L Kiessling
Journal: J Biol Chem Date: 2016-12-30 Impact factor: 5.157

5. N-methylimidazolium chloride-catalyzed pyrophosphate formation: application to the synthesis of Lipid I and NDP-sugar donors.

Authors: Hirokazu Tsukamoto; Daniel Kahne
Journal: Bioorg Med Chem Lett Date: 2011-04-22 Impact factor: 2.823

6. Alpha,beta-difluoromethylene deoxynucleoside 5'-triphosphates: a convenient synthesis of useful probes for DNA polymerase beta structure and function.

Authors: Thomas G Upton; Boris A Kashemirov; Charles E McKenna; Myron F Goodman; G K Surya Prakash; Roman Kultyshev; Vinod K Batra; David D Shock; Lars C Pedersen; William A Beard; Samuel H Wilson
Journal: Org Lett Date: 2009-05-07 Impact factor: 6.005

Improved chemical synthesis of UDP-galactofuranose.

Review 1. Targeting the formation of the cell wall core of M. tuberculosis.

2. Monitoring processivity and length control of a carbohydrate polymerase.

3. Fluorosugar chain termination agents as probes of the sequence specificity of a carbohydrate polymerase.

4. Comparing Galactan Biosynthesis in Mycobacterium tuberculosis and Corynebacterium diphtheriae.

5. N-methylimidazolium chloride-catalyzed pyrophosphate formation: application to the synthesis of Lipid I and NDP-sugar donors.

6. Alpha,beta-difluoromethylene deoxynucleoside 5'-triphosphates: a convenient synthesis of useful probes for DNA polymerase beta structure and function.

7. A single UDP-galactofuranose transporter is required for galactofuranosylation in Aspergillus fumigatus.

8. UDP-galactopyranose mutase in nematodes.

9. Potent ligands for prokaryotic UDP-galactopyranose mutase that exploit an enzyme subsite.

10. Substrate and product analogues as human O-GlcNAc transferase inhibitors.