Literature DB >> 15330636

A practical method for the stereoselective generation of beta-2-deoxy glycosyl phosphates.

Markus Oberthür1, Catherine Leimkuhler, Daniel Kahne.   

Abstract

Beta-2-Deoxy sugar nucleotides are substrates used by a variety of glycosyltransferases (Gtfs). We have developed a chemical route to synthesize beta-2-deoxy sugar phosphates that starts from alpha-glycosyl chlorides. Our approach reliably provides access to a range of NDP beta-2-deoxy sugars essential for studying glycosyltransferases involved in the synthesis of biologically active natural products. Copyright 2004 American Chemical Society

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Year:  2004        PMID： 15330636     DOI： 10.1021/ol049187f

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


  9 in total

1.  Total syntheses and initial evaluation of [Ψ[C(═S)NH]Tpg⁴]vancomycin, [Ψ[C(═NH)NH]Tpg⁴]vancomycin, [Ψ[CH₂NH]Tpg⁴]vancomycin, and their (4-chlorobiphenyl)methyl derivatives: synergistic binding pocket and peripheral modifications for the glycopeptide antibiotics.

Authors:  Akinori Okano; Atsushi Nakayama; Kejia Wu; Erick A Lindsey; Alex W Schammel; Yiqing Feng; Karen C Collins; Dale L Boger
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

2.  Next-Generation Total Synthesis of Vancomycin.

Authors:  Maxwell J Moore; Shiwei Qu; Ceheng Tan; Yu Cai; Yuzo Mogi; D Jamin Keith; Dale L Boger
Journal:  J Am Chem Soc       Date:  2020-09-04       Impact factor: 15.419

Review 3.  Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues.

Authors:  Akinori Okano; Nicholas A Isley; Dale L Boger
Journal:  Chem Rev       Date:  2017-04-24       Impact factor: 60.622

4.  A unifying nitrososynthase involved in nitrosugar biosynthesis.

Authors:  Yunfeng Hu; Ahmad Al-Mestarihi; Catherine L Grimes; Daniel Kahne; Brian O Bachmann
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

5.  C2'-OH of amphotericin B plays an important role in binding the primary sterol of human cells but not yeast cells.

Authors:  Brandon C Wilcock; Matthew M Endo; Brice E Uno; Martin D Burke
Journal:  J Am Chem Soc       Date:  2013-06-03       Impact factor: 15.419

6.  Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A.

Authors:  Catherine Leimkuhler; Micha Fridman; Tania Lupoli; Suzanne Walker; Christopher T Walsh; Daniel Kahne
Journal:  J Am Chem Soc       Date:  2007-08-08       Impact factor: 15.419

7.  Enzymatic glycosylation of vancomycin aglycon: completion of a total synthesis of vancomycin and N- and C-terminus substituent effects of the aglycon substrate.

Authors:  Atsushi Nakayama; Akinori Okano; Yiqing Feng; James C Collins; Karen C Collins; Christopher T Walsh; Dale L Boger
Journal:  Org Lett       Date:  2014-06-23       Impact factor: 6.005

8.  Synthesis and biological evaluation of prodrugs of 2-fluoro-2-deoxyribose-1-phosphate and 2,2-difluoro-2-deoxyribose-1-phosphate.

Authors:  Nadege Hamon; Maurizio Quintiliani; Jan Balzarini; Christopher McGuigan
Journal:  Bioorg Med Chem Lett       Date:  2013-03-14       Impact factor: 2.823

Review 9.  Synthesis of selected unnatural sugar nucleotides for biotechnological applications.

Authors:  Meng Qiao; Bingzhi Li; Yuan Ji; Lei Lin; Robert Linhardt; Xing Zhang
Journal:  Crit Rev Biotechnol       Date:  2020-11-05       Impact factor: 8.429
  9 in total

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