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Literature DB >> 24412338

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE.

Tiehai Li¹, Liuqing Wen¹, Adriel Williams¹, Baolin Wu¹, Lei Li¹, Jingyao Qu¹, Jeffrey Meisner¹, Zhongying Xiao¹, Junqiang Fang², Peng George Wang³.

Abstract

An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose (ADP-d, d-heptose) was reported using chemically synthesized d, d-heptose-7-phosphate and the ADP-d, d-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.

Entities: CellLine Chemical Disease Species

Keywords: Analogs; Chemoenzymatic; Specificity; Synthesis

Mesh：

Substances：

Year: 2013 PMID： 24412338 PMCID： PMC3976583 DOI： 10.1016/j.bmc.2013.12.019

Source DB: PubMed Journal: Bioorg Med Chem ISSN： 0968-0896 Impact factor: 3.641

22 in total

1. Biosynthesis of nucleotide-activated D-glycero-D-manno-heptose.

Authors: B Kneidinger; M Graninger; M Puchberger; P Kosma; P Messner
Journal: J Biol Chem Date: 2001-03-28 Impact factor: 5.157

2. A chemoenzymatic route to N-acetylglucosamine-1-phosphate analogues: substrate specificity investigations of N-acetylhexosamine 1-kinase.

Authors: Li Cai; Wanyi Guan; Motomitsu Kitaoka; Jie Shen; Chengfeng Xia; Wenlan Chen; Peng George Wang
Journal: Chem Commun (Camb) Date: 2009-04-24 Impact factor: 6.222

3. Biosynthesis pathway of ADP-L-glycero-beta-D-manno-heptose in Escherichia coli.

Authors: Bernd Kneidinger; Cristina Marolda; Michael Graninger; Alla Zamyatina; Fiona McArthur; Paul Kosma; Miguel A Valvano; Paul Messner
Journal: J Bacteriol Date: 2002-01 Impact factor: 3.490

4. The lipopolysaccharide barrier: correlation of antibiotic susceptibility with antibiotic permeability and fluorescent probe binding kinetics.

Authors: D S Snyder; T J McIntosh
Journal: Biochemistry Date: 2000-09-26 Impact factor: 3.162

5. Chemical synthesis of a bisphosphorylated mannose-6-phosphate N-glycan and its facile monoconjugation with human carbonic anhydrase II for in vivo fluorescence imaging.

Authors: Yunpeng Liu; Yan Mei Chan; Jianhui Wu; Chen Chen; Alan Benesi; Jing Hu; Yanming Wang; Gong Chen
Journal: Chembiochem Date: 2011-02-18 Impact factor: 3.164

10. Isolation of adenosine 5'-diphosphate-D-glycero-D-mannoheptose. An intermediate in lipopolysaccharide biosynthesis of Shigella sonnei.

Authors: T Kontrohr; B Kocsis
Journal: J Biol Chem Date: 1981-08-10 Impact factor: 5.157

1 in total

1. Synthesis of high-mannose oligosaccharides containing mannose-6-phosphate residues using regioselective glycosylation.

Authors: Bo Meng; Jun Wang; Quanli Wang; Anthony S Serianni; Qingfeng Pan
Journal: Carbohydr Res Date: 2018-07-31 Impact factor: 2.104

1 in total

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE.

1. Biosynthesis of nucleotide-activated D-glycero-D-manno-heptose.

2. A chemoenzymatic route to N-acetylglucosamine-1-phosphate analogues: substrate specificity investigations of N-acetylhexosamine 1-kinase.

3. Biosynthesis pathway of ADP-L-glycero-beta-D-manno-heptose in Escherichia coli.

4. The lipopolysaccharide barrier: correlation of antibiotic susceptibility with antibiotic permeability and fluorescent probe binding kinetics.

5. Chemical synthesis of a bisphosphorylated mannose-6-phosphate N-glycan and its facile monoconjugation with human carbonic anhydrase II for in vivo fluorescence imaging.

6. Modular synthesis of heparan sulfate oligosaccharides for structure-activity relationship studies.

7. A convenient synthesis of GDP D-glycero-alpha-D-manno-heptopyranose.

8. The mechanism of the reaction catalyzed by ADP-beta-L-glycero-D-manno-heptose 6-epimerase.

9. Synthesis of mono- and dideoxygenated alpha,alpha-trehalose analogs.

10. Isolation of adenosine 5'-diphosphate-D-glycero-D-mannoheptose. An intermediate in lipopolysaccharide biosynthesis of Shigella sonnei.

1. Synthesis of high-mannose oligosaccharides containing mannose-6-phosphate residues using regioselective glycosylation.