Literature DB >> 19203234

Efficient synthesis of sugar oxazolines from unprotected N-acetyl-2-amino sugars by using chloroformamidinium reagent in water.

Masato Noguchi1, Tomonari Tanaka, Hidetoshi Gyakushi, Atsushi Kobayashi, Shin-ichiro Shoda.   

Abstract

Sugar oxazoline derivatives were directly synthesized from the corresponding N-acetyl-2-amino sugars in aqueous media by using a chloroformamidinium-type dehydrating reagent. The present method could successfully be applied to chito-oligosaccharides, saccharides with acid functions, and a complex-type oligosaccharide derived from a glycopeptide.

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Year:  2009        PMID： 19203234     DOI： 10.1021/jo8024708

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


  42 in total

1.  Chemoenzymatic synthesis and Fcγ receptor binding of homogeneous glycoforms of antibody Fc domain. Presence of a bisecting sugar moiety enhances the affinity of Fc to FcγIIIa receptor.

Authors:  Guozhang Zou; Hirofumi Ochiai; Wei Huang; Qiang Yang; Cishan Li; Lai-Xi Wang
Journal:  J Am Chem Soc       Date:  2011-11-01       Impact factor: 15.419

2.  Convergent synthesis of homogeneous Glc1Man9GlcNAc2-protein and derivatives as ligands of molecular chaperones in protein quality control.

Authors:  Mohammed N Amin; Wei Huang; Rahman M Mizanur; Lai-Xi Wang
Journal:  J Am Chem Soc       Date:  2011-08-19       Impact factor: 15.419

Review 3.  Structural insights into the mechanisms and specificities of IgG-active endoglycosidases.

Authors:  Jonathan J Du; Erik H Klontz; Marcelo E Guerin; Beatriz Trastoy; Eric J Sundberg
Journal:  Glycobiology       Date:  2020-03-20       Impact factor: 4.313

4.  Site-selective chemoenzymatic glycoengineering of Fab and Fc glycans of a therapeutic antibody.

Authors:  John P Giddens; Joseph V Lomino; David J DiLillo; Jeffrey V Ravetch; Lai-Xi Wang
Journal:  Proc Natl Acad Sci U S A       Date:  2018-11-05       Impact factor: 11.205

5.  Arthrobacter endo-beta-N-acetylglucosaminidase shows transglycosylation activity on complex-type N-glycan oxazolines: one-pot conversion of ribonuclease B to sialylated ribonuclease C.

Authors:  Wei Huang; Qiang Yang; Midori Umekawa; Kenji Yamamoto; Lai-Xi Wang
Journal:  Chembiochem       Date:  2010-07-05       Impact factor: 3.164

6.  Synthetic glycopeptides as a designated standard in focused glycoproteomics to discover serum cancer biomarkers.

Authors:  K V Yogesh; Toshiya Kamiyama; Chikara Ohyama; Tohru Yoneyama; Kazuhiro Nouso; Satoshi Kimura; Hiroshi Hinou; Shin-Ichiro Nishimura
Journal:  Medchemcomm       Date:  2018-06-29       Impact factor: 3.597

7.  Endo-F3 Glycosynthase Mutants Enable Chemoenzymatic Synthesis of Core-fucosylated Triantennary Complex Type Glycopeptides and Glycoproteins.

Authors:  John P Giddens; Joseph V Lomino; Mohammed N Amin; Lai-Xi Wang
Journal:  J Biol Chem       Date:  2016-03-10       Impact factor: 5.157

Review 8.  Chemoenzymatic Methods for the Synthesis of Glycoproteins.

Authors:  Chao Li; Lai-Xi Wang
Journal:  Chem Rev       Date:  2018-08-24       Impact factor: 60.622

9.  A two-step enzymatic glycosylation of polypeptides with complex N-glycans.

Authors:  Joseph V Lomino; Andreas Naegeli; Jared Orwenyo; Mohammed N Amin; Markus Aebi; Lai-Xi Wang
Journal:  Bioorg Med Chem       Date:  2013-02-18       Impact factor: 3.641

10.  Chemoenzymatic Synthesis and Receptor Binding of Mannose-6-Phosphate (M6P)-Containing Glycoprotein Ligands Reveal Unusual Structural Requirements for M6P Receptor Recognition.

Authors:  Takahiro Yamaguchi; Mohammed N Amin; Christian Toonstra; Lai-Xi Wang
Journal:  J Am Chem Soc       Date:  2016-08-16       Impact factor: 15.419
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