Literature DB >> 20384302

Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc.

Li Cai1, Wanyi Guan, Wenlan Chen, Peng George Wang.   

Abstract

2-ketoGlc, which is the C(2)-carbon isostere of GlcNAc, is a novel GlcNAc analogue with a ketone group. The corresponding glycosyltransferase donor substrate, UDP-2-ketoGlc, is necessary for synthesizing 2-ketoGlc-containing molecules and is thus highly important for metabolic polysaccharide remodeling and engineering. We report here the first chemoenzymatic synthesis of UDP-2-ketoGlc using our two-enzyme (NahK and GlmU) system in vitro.

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Year:  2010        PMID： 20384302      PMCID： PMC2917071          DOI： 10.1021/jo100385p

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  15 in total

1.  Concerning the origin of the high beta-selectivity of glycosidation reactions of 2-deoxy-2-iodo-glucopyranosyl trichloroacetimidates.

Authors:  Pek Y Chong; William R Roush
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

2.  A chemoenzymatic approach toward the rapid and sensitive detection of O-GlcNAc posttranslational modifications.

Authors:  Nelly Khidekel; Sabine Arndt; Nathan Lamarre-Vincent; Alexander Lippert; Katherine G Poulin-Kerstien; Boopathy Ramakrishnan; Pradman K Qasba; Linda C Hsieh-Wilson
Journal:  J Am Chem Soc       Date:  2003-12-31       Impact factor: 15.419

Review 3.  Formation of the glycan chains in the synthesis of bacterial peptidoglycan.

Authors:  J van Heijenoort
Journal:  Glycobiology       Date:  2001-03       Impact factor: 4.313

4.  Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation.

Authors:  Eliana Saxon; Sarah J Luchansky; Howard C Hang; Chong Yu; Sandy C Lee; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

Review 5.  Hyaluronan.

Authors:  T C Laurent; J R Fraser
Journal:  FASEB J       Date:  1992-04       Impact factor: 5.191

6.  Enzymatic route to preparative-scale synthesis of UDP-GlcNAc/GalNAc, their analogues and GDP-fucose.

Authors:  Guohui Zhao; Wanyi Guan; Li Cai; Peng George Wang
Journal:  Nat Protoc       Date:  2010-03-11       Impact factor: 13.491

7.  Kidney N-acetylgalactosamine (GalNAc)-1-phosphate kinase, a new pathway of GalNAc activation.

Authors:  I Pastuszak; R Drake; A D Elbein
Journal:  J Biol Chem       Date:  1996-08-23       Impact factor: 5.157

8.  Improved procedure for the oxidative cleavage of olefins by OsO4-NaIO4.

Authors:  Wensheng Yu; Yan Mei; Ying Kang; Zhengmao Hua; Zhendong Jin
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

9.  A chemical approach for identifying O-GlcNAc-modified proteins in cells.

Authors:  David J Vocadlo; Howard C Hang; Eun-Ju Kim; John A Hanover; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2003-07-21       Impact factor: 11.205

10.  Identification of N-acetylhexosamine 1-kinase in the complete lacto-N-biose I/galacto-N-biose metabolic pathway in Bifidobacterium longum.

Authors:  Mamoru Nishimoto; Motomitsu Kitaoka
Journal:  Appl Environ Microbiol       Date:  2007-08-24       Impact factor: 4.792
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  5 in total

1.  Highly efficient synthesis of UDP-GalNAc/GlcNAc analogues with promiscuous recombinant human UDP-GalNAc pyrophosphorylase AGX1.

Authors:  Wanyi Guan; Li Cai; Peng George Wang
Journal:  Chemistry       Date:  2010-12-03       Impact factor: 5.236

2.  Comparing substrate specificity of two UDP-sugar pyrophosphorylases and efficient one-pot enzymatic synthesis of UDP-GlcA and UDP-GalA.

Authors:  Yuxi Guo; Junqiang Fang; Tiehai Li; Xu Li; Cheng Ma; Xuan Wang; Peng G Wang; Lei Li
Journal:  Carbohydr Res       Date:  2015-04-16       Impact factor: 2.104

3.  C2-ketonylation of carbohydrates via excited-state palladium-catalyzed 1,2-spin-center shift.

Authors:  Gaoyuan Zhao; Upasana Mukherjee; Lin Zhou; Yue Wu; Wang Yao; Jaclyn N Mauro; Peng Liu; Ming-Yu Ngai
Journal:  Chem Sci       Date:  2022-05-11       Impact factor: 9.969

4.  Fluorescein-5-thiosemicarbazide as a probe for directly imaging of mucin-type O-linked glycoprotein within living cells.

Authors:  Ying Zhang; Yujiao Sun; Zhongfu Wang; Linjuan Huang
Journal:  Glycoconj J       Date:  2012-07-15       Impact factor: 2.916

Review 5.  Bioisosteres of Carbohydrate Functional Groups in Glycomimetic Design.

Authors:  Rachel Hevey
Journal:  Biomimetics (Basel)       Date:  2019-07-28
  5 in total

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