Literature DB >> 17939723

Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations.

Adeline Miermont1, Youlin Zeng, Yuqing Jing, Xin-shan Ye, Xuefei Huang.   

Abstract

Two asymmetrically branched oligosaccharides, LewisX and dimeric LewisX, were assembled in one pot with high yields and exclusive regio- and stereoselectivities. p-Tolyl thioglycosides were utilized as the sole type of building blocks, thus simplifying the overall synthetic design. The reactivity-independent nature of the preactivation based method allows modular assembly of the dimeric LewisX octasaccharide without the need for tedious protective group manipulation to achieve exact anomeric reactivities.

Entities:  

Mesh:

Substances:

Year:  2007        PMID: 17939723      PMCID: PMC2593850          DOI: 10.1021/jo701694k

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


  19 in total

1.  Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies.

Authors:  K M Koeller; C H Wong
Journal:  Chem Rev       Date:  2000-12-13       Impact factor: 60.622

2.  Iterative one-pot synthesis of oligosaccharides.

Authors:  Xuefei Huang; Lijun Huang; Haisheng Wang; Xin-Shan Ye
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-04       Impact factor: 15.336

3.  A highly efficient synthetic strategy for polymeric support synthesis of Le(x), Le(y), and H-type 2 oligosaccharides.

Authors:  T Zhu; G J Boons
Journal:  Chemistry       Date:  2001-06-01       Impact factor: 5.236

4.  Highly efficient syntheses of hyaluronic acid oligosaccharides.

Authors:  Lijun Huang; Xuefei Huang
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

5.  Iterative one-pot syntheses of chitotetroses.

Authors:  Lijun Huang; Zhen Wang; Xiaoning Li; Xin-shan Ye; Xuefei Huang
Journal:  Carbohydr Res       Date:  2006-01-26       Impact factor: 2.104

6.  From the Laboratory to the Clinic: A Retrospective on Fully Synthetic Carbohydrate-Based Anticancer Vaccines Frequently used abbreviations are listed in the appendix.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-03       Impact factor: 15.336

7.  Synthesis of the Lewis b hexasaccharide and HSA-conjugates thereof.

Authors:  Martina Lahmann; Linnéa Bülow; Peter Teodorovic; Helena Gybäck; Stefan Oscarson
Journal:  Glycoconj J       Date:  2004       Impact factor: 2.916

8.  Automated carbohydrate synthesis to drive chemical glycomics.

Authors:  Peter H Seeberger
Journal:  Chem Commun (Camb)       Date:  2003-05-21       Impact factor: 6.222

9.  Anti-Lewis X antibody and Lewis X-anti-Lewis X immune complexes in Helicobacter pylori infection.

Authors:  M Chmiela; T Wadstrom; H Folkesson; I Płaneta Małecka; E Czkwianianc; T Rechciński; W Rudnicka
Journal:  Immunol Lett       Date:  1998-04       Impact factor: 3.685

10.  Novel fucolipids accumulating in human adenocarcinoma. II. Selective isolation of hybridoma antibodies that differentially recognize mono-, di-, and trifucosylated type 2 chain.

Authors:  Y Fukushi; S Hakomori; E Nudelman; N Cochran
Journal:  J Biol Chem       Date:  1984-04-10       Impact factor: 5.157

View more
  15 in total

1.  Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

Authors:  Youlin Zeng; Zhen Wang; Dennis Whitfield; Xuefei Huang
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

2.  Obstacles and solutions for chemical synthesis of syndecan-3 (53-62) glycopeptides with two heparan sulfate chains.

Authors:  Weizhun Yang; Keisuke Yoshida; Bo Yang; Xuefei Huang
Journal:  Carbohydr Res       Date:  2016-10-20       Impact factor: 2.104

3.  Preactivation-based, one-pot combinatorial synthesis of heparin-like hexasaccharides for the analysis of heparin-protein interactions.

Authors:  Zhen Wang; Yongmei Xu; Bo Yang; Gopinath Tiruchinapally; Bin Sun; Renpeng Liu; Steven Dulaney; Jian Liu; Xuefei Huang
Journal:  Chemistry       Date:  2010-07-26       Impact factor: 5.236

4.  Comparative immunological studies of tumor-associated Lewis X, Lewis Y, and KH-1 antigens.

Authors:  Jiatong Guo; Wenjie Jiang; Qingjiang Li; Mohit Jaiswal; Zhongwu Guo
Journal:  Carbohydr Res       Date:  2020-03-31       Impact factor: 2.104

5.  Synthesis of the Cancer-Associated KH-1 Antigen by Block Assembly of Its Backbone Structure Followed by One-Step Grafting of Three Fucose Residues.

Authors:  Qingjiang Li; Zhongwu Guo
Journal:  Org Lett       Date:  2017-11-29       Impact factor: 6.005

6.  Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

Authors:  Bo Yang; Yuqing Jing; Xuefei Huang
Journal:  European J Org Chem       Date:  2010-01-27

7.  Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides.

Authors:  Mohammed Y R Sardar; Venkata R Krishnamurthy; Simon Park; Appi Reddy Mandhapati; Walter J Wever; Dayoung Park; Richard D Cummings; Elliot L Chaikof
Journal:  Carbohydr Res       Date:  2017-10-10       Impact factor: 2.104

Review 8.  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

9.  Chemical synthesis of a heparan sulfate glycopeptide: syndecan-1.

Authors:  Bo Yang; Keisuke Yoshida; Zhaojun Yin; Hang Dai; Herbert Kavunja; Mohammad H El-Dakdouki; Suttipun Sungsuwan; Steven B Dulaney; Xuefei Huang
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-07       Impact factor: 15.336

10.  Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.

Authors:  Bin Sun; Balasubramanian Srinivasan; Xuefei Huang
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.