Literature DB >> 30559190

Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Samuel M Levi1, Qiuhan Li1, Andreas R Rötheli1, Eric N Jacobsen2.   

Abstract

Glycosyl phosphates are shown to be activated to stereospecific nucleophilic substitution reactions by precisely tailored bis-thiourea catalysts. Enhanced reactivity and scope is observed with phosphate relative to chloride leaving groups. Stronger binding (Km) to the H-bond donor and enhanced reactivity of the complex (kcat) enables efficient catalysis with broad functional group compatibility under mild, neutral conditions.

Entities:  

Keywords:  H bonding; glycosylation; organocatalysis; phosphate

Mesh：

Substances：

Year:  2018        PMID： 30559190      PMCID： PMC6320501          DOI： 10.1073/pnas.1811186116

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  23 in total

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Authors:  Helle M Christensen; Stefan Oscarson; Henrik H Jensen
Journal:  Carbohydr Res       Date:  2015-02-25       Impact factor: 2.104

Review 2.  Chiral reagents in glycosylation and modification of carbohydrates.

Authors:  Hao-Yuan Wang; Stephanie A Blaszczyk; Guozhi Xiao; Weiping Tang
Journal:  Chem Soc Rev       Date:  2018-02-05       Impact factor: 54.564

3.  Sensitive and Accurate 13C Kinetic Isotope Effect Measurements Enabled by Polarization Transfer.

Authors:  Eugene E Kwan; Yongho Park; Harrison A Besser; Thayer L Anderson; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-12-29       Impact factor: 15.419

4.  Chiral phosphoric acid-catalyzed desymmetrizative glycosylation of 2-deoxystreptamine and its application to aminoglycoside synthesis.

Authors:  Jeonghyo Lee; Alina Borovika; Yaroslav Khomutnyk; Pavel Nagorny
Journal:  Chem Commun (Camb)       Date:  2017-08-08       Impact factor: 6.222

5.  Glycosylation catalyzed by a chiral Brønsted acid.

Authors:  Daniel J Cox; Martin D Smith; Antony J Fairbanks
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

Review 6.  Aromatic O-glycosylation.

Authors:  Mårten Jacobsson; Jesper Malmberg; Ulf Ellervik
Journal:  Carbohydr Res       Date:  2006-05-02       Impact factor: 2.104

7.  α-Selective organocatalytic synthesis of 2-deoxygalactosides.

Authors:  Edward I Balmond; Diane M Coe; M Carmen Galan; Eoghan M McGarrigle
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-09       Impact factor: 15.336

8.  Cooperative catalysis in glycosidation reactions with O-glycosyl trichloroacetimidates as glycosyl donors.

Authors:  Yiqun Geng; Amit Kumar; Hassan M Faidallah; Hassan A Albar; Ibrahim A Mhkalid; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-26       Impact factor: 15.336

9.  Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid.

Authors:  Tomoya Kimura; Takahiro Eto; Daisuke Takahashi; Kazunobu Toshima
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

Review 10.  Glycosyltransferases: structures, functions, and mechanisms.

Authors:  L L Lairson; B Henrissat; G J Davies; S G Withers
Journal:  Annu Rev Biochem       Date:  2008       Impact factor: 23.643
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  9 in total

1.  Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Authors:  Qiuhan Li; Samuel M Levi; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-06-26       Impact factor: 15.419

2.  Recent Developments in Stereoselective Chemical Glycosylation.

Authors:  Jesse Ling; Clay S Bennett
Journal:  Asian J Org Chem       Date:  2019-05-02       Impact factor: 3.319

3.  Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors.

Authors:  Andrew B Mayfield; Jan B Metternich; Adam H Trotta; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2020-02-14       Impact factor: 15.419

Review 4.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

5.  Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.

Authors:  Girish C Sati; Joshua L Martin; Yishu Xu; Tanmay Malakar; Paul M Zimmerman; John Montgomery
Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419

6.  Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations.

Authors:  Ming-Hua Zhuo; David J Wilbur; Eugene E Kwan; Clay S Bennett
Journal:  J Am Chem Soc       Date:  2019-10-09       Impact factor: 15.419

7.  Hydrogen bond activated glycosylation under mild conditions.

Authors:  Ke Xiao; Yongxin Hu; Yongyong Wan; XinXin Li; Qin Nie; Hao Yan; Liming Wang; Jinxi Liao; Deyong Liu; Yuanhong Tu; Jiansong Sun; Jeroen D C Codée; Qingju Zhang
Journal:  Chem Sci       Date:  2021-12-15       Impact factor: 9.825

8.  A "Traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2-cis-Glycopyranosides.

Authors:  Xu Ma; Zhitong Zheng; Yue Fu; Xijun Zhu; Peng Liu; Liming Zhang
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 16.383

9.  Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides.

Authors:  Xiaojuan Zhang; Yutong Yang; Jiahao Ding; Yun Zhao; Hongbin Zhang; Yugen Zhu
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 17.694
  9 in total

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