Literature DB >> 18639240

Chemical preparation of sialyl Lewis x using an enzymatically synthesized sialoside building block.

Hongzhi Cao1, Shengshu Huang, Jiansong Cheng, Yanhong Li, Saddam Muthana, Bryan Son, Xi Chen.   

Abstract

The sialyl Lewis x tetrasaccharide with a propylamine aglycon was assembled by chemoselective glycosylation from a p-tolyl thioglycosyl donor obtained from an enzymatically synthesized sialodisaccharide. Combining the advantages of highly efficient enzymatic synthesis of sialoside building blocks, and diverse chemical glycosylation, this chemoenzymatic approach is practical for obtaining complex sialosides and their analogues.

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Year:  2008        PMID： 18639240      PMCID： PMC2783551          DOI： 10.1016/j.carres.2008.06.020

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  32 in total

1.  Recent advances in o-sialylation.

Authors:  G J Boons; A V Demchenko
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

2.  Selectinminus signCarbohydrate Interactions: From Natural Ligands to Designed Mimics.

Authors:  Eric E. Simanek; Glenn J. McGarvey; Jill A. Jablonowski; Chi-Huey Wong
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

Review 3.  The chemistry of oligosaccharide ligands of selectins: significance for the development of new immunomodulatory medicines.

Authors:  F M Unger
Journal:  Adv Carbohydr Chem Biochem       Date:  2001       Impact factor: 12.200

Review 4.  Regulatory roles of carbohydrate ligands for selectins in the homing of lymphocytes.

Authors:  Reiji Kannagi
Journal:  Curr Opin Struct Biol       Date:  2002-10       Impact factor: 6.809

Review 5.  Design and synthesis of sialyl Lewis(x) mimics as E- and P-selectin inhibitors.

Authors:  Neelu Kaila; Bert E Thomas
Journal:  Med Res Rev       Date:  2002-11       Impact factor: 12.944

6.  A multifunctional Pasteurella multocida sialyltransferase: a powerful tool for the synthesis of sialoside libraries.

Authors:  Hai Yu; Harshal Chokhawala; Rebekah Karpel; Hui Yu; Bingyuan Wu; Jianbo Zhang; Yingxin Zhang; Qiang Jia; Xi Chen
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

Review 7.  Synthetic carbohydrate-based antitumor vaccines: challenges and opportunities.

Authors:  Ouathek Ouerfelli; J David Warren; Rebecca M Wilson; Samuel J Danishefsky
Journal:  Expert Rev Vaccines       Date:  2005-10       Impact factor: 5.217

Review 8.  Synthesis and medical applications of oligosaccharides.

Authors:  Peter H Seeberger; Daniel B Werz
Journal:  Nature       Date:  2007-04-26       Impact factor: 49.962

9.  Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors.

Authors:  Zhen Wang; Luyuan Zhou; Kheireddine El-Boubbou; Xin-shan Ye; Xuefei Huang
Journal:  J Org Chem       Date:  2007-07-21       Impact factor: 4.354

Review 10.  The discovery, biology, and drug development of sialyl Lea and sialyl Lex.

Authors:  John L Magnani
Journal:  Arch Biochem Biophys       Date:  2004-06-15       Impact factor: 4.013
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  13 in total

1.  Cloning and characterization of a viral α2-3-sialyltransferase (vST3Gal-I) for the synthesis of sialyl Lewisx.

Authors:  Go Sugiarto; Kam Lau; Hai Yu; Stephanie Vuong; Vireak Thon; Yanhong Li; Shengshu Huang; Xi Chen
Journal:  Glycobiology       Date:  2010-10-26       Impact factor: 4.313

2.  Chemoenzymatic synthesis of α2-3-sialylated carbohydrate epitopes.

Authors:  Huang Shengshu; Yu Hai; Chen Xi
Journal:  Sci China Chem       Date:  2011-01       Impact factor: 9.445

Review 3.  Advances in the biology and chemistry of sialic acids.

Authors:  Xi Chen; Ajit Varki
Journal:  ACS Chem Biol       Date:  2010-02-19       Impact factor: 5.100

4.  Chemoenzymatic synthesis of α-dystroglycan core M1 O-mannose glycans.

Authors:  Yan Zhang; Caicai Meng; Lan Jin; Xi Chen; Fengshan Wang; Hongzhi Cao
Journal:  Chem Commun (Camb)       Date:  2015-06-23       Impact factor: 6.222

Review 5.  Sialic acid metabolism and sialyltransferases: natural functions and applications.

Authors:  Yanhong Li; Xi Chen
Journal:  Appl Microbiol Biotechnol       Date:  2012-04-13       Impact factor: 4.813

Review 6.  Recent progress in chemical and chemoenzymatic synthesis of carbohydrates.

Authors:  Saddam Muthana; Hongzhi Cao; Xi Chen
Journal:  Curr Opin Chem Biol       Date:  2009-10-14       Impact factor: 8.822

7.  Ultrasound Detection of Myocardial Ischemic Memory Using an E-Selectin Targeting Peptide Amenable to Human Application.

Authors:  Xiaoping Leng; Jianjun Wang; Andrew Carson; Xucai Chen; Huili Fu; Susanne Ottoboni; William R Wagner; Flordeliza S Villanueva
Journal:  Mol Imaging       Date:  2014-04-01       Impact factor: 4.488

8.  One-pot multienzyme (OPME) systems for chemoenzymatic synthesis of carbohydrates.

Authors:  Hai Yu; Xi Chen
Journal:  Org Biomol Chem       Date:  2016-03-14       Impact factor: 3.876

9.  Parallel chemoenzymatic synthesis of sialosides containing a C5-diversified sialic acid.

Authors:  Hongzhi Cao; Saddam Muthana; Yanhong Li; Jiansong Cheng; Xi Chen
Journal:  Bioorg Med Chem Lett       Date:  2009-08-26       Impact factor: 2.823

10.  A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides.

Authors:  Abhishek Santra; An Xiao; Hai Yu; Wanqing Li; Yanhong Li; Linh Ngo; John B McArthur; Xi Chen
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-14       Impact factor: 15.336
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