Literature DB >> 28302960

Development of chemical and chemo-enzymatic glycosylations.

Shin-Ichiro Shoda1.   

Abstract

Glycosidic compounds are indispensable molecules in living systems. Biological phenomena such as cell wall formation, energy storage, and cell recognition strongly depend on the multi-functional characters of these substances. Development of highly regio- and stereoselective glycosylation reactions is necessary to provide sufficient amounts of specific compounds in basic research as well as for applications in industry. This review presents an overview of chemical and chemo-enzymatic n class="Chemical">glycosylations that have been developed during my forty-year academic career in the field of glyco-science. In the course of these studies, several new concepts such as "Direct Anomeric Activation", "Glyco-Process Chemistry" and "Glyco-Chemistry Cycles" have been established.

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Year:  2017        PMID： 28302960      PMCID： PMC5422579          DOI： 10.2183/pjab.93.008

Source DB:  PubMed          Journal:  Proc Jpn Acad Ser B Phys Biol Sci        ISSN： 0386-2208            Impact factor:   3.493


  17 in total

1.  Efficient transfer of sialo-oligosaccharide onto proteins by combined use of a glycosynthase-like mutant of Mucor hiemalis endoglycosidase and synthetic sialo-complex-type sugar oxazoline.

Authors:  Midori Umekawa; Takayuki Higashiyama; Yurie Koga; Tomonari Tanaka; Masato Noguchi; Atsushi Kobayashi; Shin-Ichiro Shoda; Wei Huang; Lai-Xi Wang; Hisashi Ashida; Kenji Yamamoto
Journal:  Biochim Biophys Acta       Date:  2010-07-18

2.  Remarkable transglycosylation activity of glycosynthase mutants of endo-D, an endo-β-N-acetylglucosaminidase from Streptococcus pneumoniae.

Authors:  Shu-Quan Fan; Wei Huang; Lai-Xi Wang
Journal:  J Biol Chem       Date:  2012-02-08       Impact factor: 5.157

3.  Stereospecific synthesis of 1,2-cis glycosides by allyl-mediated intramolecular aglycon delivery. 2. The use of glycosyl fluorides.

Authors:  I Cumpstey; A J Fairbanks; A J Redgrave
Journal:  Org Lett       Date:  2001-07-26       Impact factor: 6.005

4.  An endoglycosidase with alternative glycan specificity allows broadened glycoprotein remodelling.

Authors:  Jonathan J Goodfellow; Kavitha Baruah; Keisuke Yamamoto; Camille Bonomelli; Benjamin Krishna; David J Harvey; Max Crispin; Christopher N Scanlan; Benjamin G Davis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

5.  Total synthesis of agelagalastatin.

Authors:  Yong Joo Lee; Bo-Young Lee; Heung Bae Jeon; Kwan Soo Kim
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

6.  A novel disaccharide substrate having 1,2-oxazoline moiety for detection of transglycosylating activity of endoglycosidases.

Authors:  M Fujita; S Shoda; K Haneda; T Inazu; K Takegawa; K Yamamoto
Journal:  Biochim Biophys Acta       Date:  2001-09-03

7.  A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis: 4,6-dimethoxy-1,3,5-triazin-2-yl glycoside.

Authors:  Tomonari Tanaka; Masato Noguchi; Atsushi Kobayashi; Shin-Ichiro Shoda
Journal:  Chem Commun (Camb)       Date:  2008-03-03       Impact factor: 6.222

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

Authors:  Masato Noguchi; Tomonari Tanaka; Hidetoshi Gyakushi; Atsushi Kobayashi; Shin-ichiro Shoda
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

9.  One-step conversion of unprotected sugars to beta-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution.

Authors:  Tomonari Tanaka; Hikaru Nagai; Masato Noguchi; Atsushi Kobayashi; Shin-Ichiro Shoda
Journal:  Chem Commun (Camb)       Date:  2009-05-13       Impact factor: 6.222

10.  Glycoengineered Monoclonal Antibodies with Homogeneous Glycan (M3, G0, G2, and A2) Using a Chemoenzymatic Approach Have Different Affinities for FcγRIIIa and Variable Antibody-Dependent Cellular Cytotoxicity Activities.

Authors:  Masaki Kurogochi; Masako Mori; Kenji Osumi; Mami Tojino; Shu-Ichi Sugawara; Shou Takashima; Yuriko Hirose; Wataru Tsukimura; Mamoru Mizuno; Junko Amano; Akio Matsuda; Masahiro Tomita; Atsushi Takayanagi; Shin-Ichiro Shoda; Takashi Shirai
Journal:  PLoS One       Date:  2015-07-22       Impact factor: 3.240
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  1 in total

1.  Synthesis and Aggregation Behavior of Temperature- and pH-Responsive Glycopolymers as Sugar-Displaying Conjugates.

Authors:  Sotaro Tsuji; Tomohiro Aoki; Shunsuke Ushio; Tomonari Tanaka
Journal:  Polymers (Basel)       Date:  2020-04-20       Impact factor: 4.329
  1 in total

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