Literature DB >> 22924154

Recent Advances in Transition Metal-Catalyzed Glycosylation.

Matthew J McKay1, Hien M Nguyen.   

Abstract

Having access to mild and operationally simple techniques for attaining carbohydrate targets will be necessary to facilitate advancement in biological, medicinal, and pharmacological research. Even with the abundance of elegant reports for generating glycosidic linkages, stereoselective construction of α- and β-oligosaccharides and glycoconjugates is by no means trivial. In an era where expanded awareness of the impact we are having on the environment drives the state-of-the-art, synthetic chemists are tasked with developing cleaner and more efficient reactions for achieving their transformations. This movement imparts the value that prevention of waste is always superior to its treatment or cleanup. This review will highlight recent advancement in this regard by examining strategies that employ transition metal catalysis in the synthesis of oligosaccharides and glycoconjugates. These methods are mild and effective for constructing glycosidic bonds with reduced levels of waste through utilization of sub-stoichiometric amounts of transition metals to promote the glycosylation.

Entities:  

Year:  2012        PMID: 22924154      PMCID: PMC3423999          DOI: 10.1021/cs3002513

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  126 in total

Review 1.  Novel glycosylation methods and their application to natural products synthesis.

Authors:  Kazunobu Toshima
Journal:  Carbohydr Res       Date:  2006-04-21       Impact factor: 2.104

2.  Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: an entry to functionalized gamma-lactones.

Authors:  Emilie Genin; Patrick Yves Toullec; Sylvain Antoniotti; Célia Brancour; Jean-Pierre Genêt; Véronique Michelet
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419

3.  Combinatorial synthesis of deoxyhexasaccharides related to the landomycin A sugar moiety, based on an orthogonal deprotection strategy.

Authors:  Hiroshi Tanaka; Sho Yamaguchi; Atsushi Yoshizawa; Motoki Takagi; Kazuo Shin-ya; Takashi Takahashi
Journal:  Chem Asian J       Date:  2010-06-01

4.  Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors.

Authors:  Ashif Y Shaikh; Gopalsamy Sureshkumar; Debasish Pati; Sayam Sen Gupta; Srinivas Hotha
Journal:  Org Biomol Chem       Date:  2011-04-12       Impact factor: 3.876

5.  Landomycin A inhibits DNA synthesis and G1/S cell cycle progression.

Authors:  R T Crow; B Rosenbaum; R Smith; Y Guo; K S Ramos; G A Sulikowski
Journal:  Bioorg Med Chem Lett       Date:  1999-06-21       Impact factor: 2.823

6.  Synthesis and Evaluation of the α-D-/α-L-Rhamnosyl and Amicetosyl Digitoxigenin Oligomers as Anti-tumor Agents.

Authors:  Hua-Yu Leo Wang; Yon Rojanasakul; George A O'Doherty
Journal:  ACS Med Chem Lett       Date:  2011-04-14       Impact factor: 4.345

Review 7.  Beta-N-acetylhexosaminidase: a target for the design of antifungal agents.

Authors:  M Horsch; C Mayer; U Sennhauser; D M Rast
Journal:  Pharmacol Ther       Date:  1997 Oct-Dec       Impact factor: 12.310

8.  Direct and stereoselective synthesis of alpha-linked 2-deoxyglycosides.

Authors:  Jin Park; Thomas J Boltje; Geert-Jan Boons
Journal:  Org Lett       Date:  2008-09-03       Impact factor: 6.005

9.  D-Penturonic acids: solution studies of stable-isotopically enriched compounds by 1H- and 13C-n.m.r. spectroscopy.

Authors:  J A Wu; A S Serianni
Journal:  Carbohydr Res       Date:  1991-03-20       Impact factor: 2.104

10.  De novo synthesis of the trisaccharide subunit of landomycins A and E.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  Org Lett       Date:  2008-05-08       Impact factor: 6.005

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  29 in total

Review 1.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 2.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

3.  Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor.

Authors:  Zhitong Zheng; Liming Zhang
Journal:  Carbohydr Res       Date:  2018-10-26       Impact factor: 2.104

4.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  RSC Adv       Date:  2016-11-24       Impact factor: 3.361

5.  Scalable synthesis of Fmoc-protected GalNAc-threonine amino acid and T(N) antigen via nickel catalysis.

Authors:  Fei Yu; Matthew S McConnell; Hien M Nguyen
Journal:  Org Lett       Date:  2015-04-08       Impact factor: 6.005

6.  Regenerative Glycosylation.

Authors:  Yashapal Singh; Tinghua Wang; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2017-12-22       Impact factor: 4.354

7.  Advances in the Chemical Synthesis of Carbohydrates and Glycoconjugates.

Authors:  Ankita Malik; Peter H Seeberger; Daniel Varón Silva
Journal:  Adv Biochem Eng Biotechnol       Date:  2021       Impact factor: 2.635

8.  Utilization of bench-stable and readily available nickel(II) triflate for access to 1,2-cis-2-aminoglycosides.

Authors:  Eric T Sletten; Sai Kumar Ramadugu; Hien M Nguyen
Journal:  Carbohydr Res       Date:  2016-10-24       Impact factor: 2.104

9.  Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

Authors:  Guillaume Pelletier; Aaron Zwicker; C Liana Allen; Alanna Schepartz; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-03-01       Impact factor: 15.419

10.  β-Mannosylation via O-Alkylation of Anomeric Cesium Alkoxides: Mechanistic Studies and Synthesis of the Hexasaccharide Core of Complex Fucosylated N-Linked Glycans.

Authors:  Shuai Meng; Bishwa Raj Bhetuwal; Hai Nguyen; Xiaotian Qi; Cheng Fang; Kevin Saybolt; Xiaohua Li; Peng Liu; Jianglong Zhu
Journal:  European J Org Chem       Date:  2020-03-19
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