Literature DB >> 30843692

Redox-Controlled Site-Specific α2-6-Sialylation.

Na Lu1, Jinfeng Ye1, Jiansong Cheng2, Aniruddha Sasmal3, Chang-Cheng Liu1,4, Wenlong Yao1, Jun Yan1, Naazneen Khan3, Wen Yi5, Ajit Varki3, Hongzhi Cao1,4.   

Abstract

The first bacterial α2-6-sialyltransferase cloned from Photobacterium damselae (Pd2,6ST) has been widely applied for the synthesis of various α2-6-linked sialosides. However, the extreme substrate flexibility of Pd2,6ST makes it unsuitable for site-specific α2-6-sialylation of complex substrates containing multiple galactose and/or N-acetylgalactosamine units. To tackle this problem, a general redox-controlled site-specific sialylation strategy using Pd2,6ST is described. This approach features site-specific enzymatic oxidation of galactose units to mask the unwanted sialylation sites and precisely controlling the site-specific α2-6-sialylation at intact galactose or N-acetylgalactosamine units.

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Year:  2019        PMID： 30843692      PMCID： PMC7239639          DOI： 10.1021/jacs.9b00044

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  52 in total

1.  Synthesis of asymmetrical multiantennary human milk oligosaccharides.

Authors:  Anthony R Prudden; Lin Liu; Chantelle J Capicciotti; Margreet A Wolfert; Shuo Wang; Zhongwei Gao; Lu Meng; Kelley W Moremen; Geert-Jan Boons
Journal:  Proc Natl Acad Sci U S A       Date:  2017-06-19       Impact factor: 11.205

2.  Characterization and synthetic application of a novel beta1,3-galactosyltransferase from Escherichia coli O55:H7.

Authors:  Xian-wei Liu; Chengfeng Xia; Lei Li; Wan-yi Guan; Nicholas Pettit; Hou-cheng Zhang; Min Chen; Peng George Wang
Journal:  Bioorg Med Chem       Date:  2009-06-09       Impact factor: 3.641

3.  Sequential one-pot enzymatic synthesis of oligo-N-acetyllactosamine and its multi-sialylated extensions.

Authors:  Wei-Ting Chien; Chien-Fu Liang; Ching-Ching Yu; Chien-Hung Lin; Si-Peng Li; Indah Primadona; Yu-Ju Chen; Kwok Kong T Mong; Chun-Cheng Lin
Journal:  Chem Commun (Camb)       Date:  2014-04-22       Impact factor: 6.222

4.  Combination of automated solid-phase and enzymatic oligosaccharide synthesis provides access to α(2,3)-sialylated glycans.

Authors:  Richard J Fair; Heung Sik Hahm; Peter H Seeberger
Journal:  Chem Commun (Camb)       Date:  2015-04-11       Impact factor: 6.222

5.  Biosynthesis of ganglioside mimics in Campylobacter jejuni OH4384. Identification of the glycosyltransferase genes, enzymatic synthesis of model compounds, and characterization of nanomole amounts by 600-mhz (1)h and (13)c NMR analysis.

Authors:  M Gilbert; J R Brisson; M F Karwaski; J Michniewicz; A M Cunningham; Y Wu; N M Young; W W Wakarchuk
Journal:  J Biol Chem       Date:  2000-02-11       Impact factor: 5.157

6.  Chemoenzymatic synthesis of GD3 oligosaccharides and other disialyl glycans containing natural and non-natural sialic acids.

Authors:  Hai Yu; Jiansong Cheng; Li Ding; Zahra Khedri; Yi Chen; Sharlene Chin; Kam Lau; Vinod Kumar Tiwari; Xi Chen
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

7.  The carbohydrate of bovine prothrombin. Occurrence of Gal beta 1 leads to 3GlcNAc grouping in asparagine-linked sugar chains.

Authors:  T Mizuochi; K Yamashita; K Fujikawa; W Kisiel; A Kobata
Journal:  J Biol Chem       Date:  1979-07-25       Impact factor: 5.157

8.  Single amino acid substitutions in influenza haemagglutinin change receptor binding specificity.

Authors:  G N Rogers; J C Paulson; R S Daniels; J J Skehel; I A Wilson; D C Wiley
Journal:  Nature       Date:  1983 Jul 7-13       Impact factor: 49.962

9.  Gangliosides are neuronal ligands for myelin-associated glycoprotein.

Authors:  L J Yang; C B Zeller; N L Shaper; M Kiso; A Hasegawa; R E Shapiro; R L Schnaar
Journal:  Proc Natl Acad Sci U S A       Date:  1996-01-23       Impact factor: 11.205

10.  Synthesis of disialoganglioside GD1 alpha and its positional isomer.

Authors:  H Prabhanjan; K Aoyama; M Kiso; A Hasegawa
Journal:  Carbohydr Res       Date:  1992-09-02       Impact factor: 2.104
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  4 in total

1.  Biochemical characterization of Helicobacter pylori α1-3-fucosyltransferase and its application in the synthesis of fucosylated human milk oligosaccharides.

Authors:  Jing Bai; Zhigang Wu; Go Sugiarto; Madhusudhan Reddy Gadi; Hai Yu; Yanhong Li; Cong Xiao; Alice Ngo; Baohua Zhao; Xi Chen; Wanyi Guan
Journal:  Carbohydr Res       Date:  2019-05-16       Impact factor: 2.104

Review 2.  Recent progress in synthesis of carbohydrates with sugar nucleotide-dependent glycosyltransferases.

Authors:  Lan Na; Riyao Li; Xi Chen
Journal:  Curr Opin Chem Biol       Date:  2020-12-10       Impact factor: 8.822

3.  Sialoglycan-binding patterns of bacterial AB5 toxin B subunits correlate with host range and toxicity, indicating evolution independent of A subunits.

Authors:  Naazneen Khan; Aniruddha Sasmal; Zahra Khedri; Patrick Secrest; Andrea Verhagen; Saurabh Srivastava; Nissi Varki; Xi Chen; Hai Yu; Travis Beddoe; Adrienne W Paton; James C Paton; Ajit Varki
Journal:  J Biol Chem       Date:  2022-04-07       Impact factor: 5.486

4.  Evolution of Human-Specific Alleles Protecting Cognitive Function of Grandmothers.

Authors:  Sudeshna Saha; Naazneen Khan; Troy Comi; Andrea Verhagen; Aniruddha Sasmal; Sandra Diaz; Hai Yu; Xi Chen; Joshua M Akey; Martin Frank; Pascal Gagneux; Ajit Varki
Journal:  Mol Biol Evol       Date:  2022-08-03       Impact factor: 8.800
  4 in total

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