Literature DB >> 31585319

The chemical synthesis of human milk oligosaccharides: Lacto-N-tetraose (Galβ1→3GlcNAcβ1→3Galβ1→4Glc).

Mithila D Bandara1, Keith J Stine1, Alexei V Demchenko2.   

Abstract

The total chemical synthesis of lacto-N-tetraose (LNT) has been completed using both convergent and linear strategies. Similarly to that of our previous HMO syntheses, the donor-acceptor protecting-leaving group combinations were found to be of paramount significance to achieving successful glycosylations and minimizing side reactions.
Copyright © 2019 Elsevier Ltd. All rights reserved.

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Year:  2019        PMID： 31585319      PMCID： PMC6897367          DOI： 10.1016/j.carres.2019.107824

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  23 in total

1.  Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Authors:  Laurel K Mydock; Alexei V Demchenko
Journal:  Org Lett       Date:  2008-05-01       Impact factor: 6.005

2.  Mechanistic studies and methods to prevent aglycon transfer of thioglycosides.

Authors:  Zhitao Li; Jeffrey C Gildersleeve
Journal:  J Am Chem Soc       Date:  2006-09-06       Impact factor: 15.419

3.  Chemoenzymatic Synthesis of a Library of Human Milk Oligosaccharides.

Authors:  Zhongying Xiao; Yuxi Guo; Yunpeng Liu; Lei Li; Qing Zhang; Liuqing Wen; Xuan Wang; Shukkoor Muhammed Kondengaden; Zhigang Wu; Jun Zhou; Xuefeng Cao; Xu Li; Cheng Ma; Peng George Wang
Journal:  J Org Chem       Date:  2016-06-29       Impact factor: 4.354

Review 4.  Human milk oligosaccharides and infant gut bifidobacteria: Molecular strategies for their utilization.

Authors:  Pamela Thomson; Daniel A Medina; Daniel Garrido
Journal:  Food Microbiol       Date:  2017-09-04       Impact factor: 5.516

5.  Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.

Authors:  Pavel Nagorny; Bernhard Fasching; Xuechen Li; Gong Chen; Baptiste Aussedat; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

Review 6.  Human Milk Nutrient Composition in the United States: Current Knowledge, Challenges, and Research Needs.

Authors:  Xianli Wu; Robert T Jackson; Saira A Khan; Jaspreet Ahuja; Pamela R Pehrsson
Journal:  Curr Dev Nutr       Date:  2018-05-31

Review 7.  Structure-function relationships of human milk oligosaccharides.

Authors:  Lars Bode; Evelyn Jantscher-Krenn
Journal:  Adv Nutr       Date:  2012-05-01       Impact factor: 8.701

8.  Creating a Mass Spectral Reference Library for Oligosaccharides in Human Milk.

Authors:  Connie A Remoroza; Tytus D Mak; Maria Lorna A De Leoz; Yuri A Mirokhin; Stephen E Stein
Journal:  Anal Chem       Date:  2018-07-17       Impact factor: 6.986

9.  Human milk oligosaccharides, milk microbiome and infant gut microbiome modulate neonatal rotavirus infection.

Authors:  Sasirekha Ramani; Christopher J Stewart; Daniel R Laucirica; Nadim J Ajami; Bianca Robertson; Chloe A Autran; Dhairyasheel Shinge; Sandya Rani; Sasirekha Anandan; Liya Hu; Josephine C Ferreon; Kurien A Kuruvilla; Joseph F Petrosino; B V Venkataram Prasad; Lars Bode; Gagandeep Kang; Mary K Estes
Journal:  Nat Commun       Date:  2018-11-27       Impact factor: 14.919

Review 10.  Human Milk Oligosaccharides (HMOS): Structure, Function, and Enzyme-Catalyzed Synthesis.

Authors:  Xi Chen
Journal:  Adv Carbohydr Chem Biochem       Date:  2015-11-11       Impact factor: 3.714
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  10 in total

1.  Like mother, like microbe: human milk oligosaccharide mediated microbiome symbiosis.

Authors:  Schuyler A Chambers; Steven D Townsend
Journal:  Biochem Soc Trans       Date:  2020-06-30       Impact factor: 5.407

2.  Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal.

Authors:  Scott A Geringer; Michael P Mannino; Mithila D Bandara; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2020-07-01       Impact factor: 3.876

3.  Chemical Synthesis of Human Milk Oligosaccharides: Lacto-N-hexaose Galβ1→3GlcNAcβ1→3 [Galβ1→4GlcNAcβ1→6] Galβ1→4Glc.

Authors:  Mithila D Bandara; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2019-12-05       Impact factor: 4.354

4.  HPLC-Based Automated Synthesis of Glycans in Solution.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2022-05-25       Impact factor: 5.020

5.  Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto-N-Hexaose.

Authors:  Kai-Eng Ooi; Xiu-Wen Zhang; Cheng-Yu Kuo; Ying-Jia Liu; Ching-Ching Yu
Journal:  Front Chem       Date:  2022-05-31       Impact factor: 5.545

6.  Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides.

Authors:  Hayley B Steber; Yashapal Singh; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2021-03-24       Impact factor: 3.876

7.  Palladium(II)-assisted activation of thioglycosides.

Authors:  Samira Escopy; Yashapal Singh; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2021-03-11       Impact factor: 3.876

8.  Substrate and Process Engineering for Biocatalytic Synthesis and Facile Purification of Human Milk Oligosaccharides.

Authors:  Yuanyuan Bai; Xiaohong Yang; Hai Yu; Xi Chen
Journal:  ChemSusChem       Date:  2022-02-18       Impact factor: 9.140

9.  A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2020-11-30       Impact factor: 5.236

Review 10.  Anti-Angiogenic Property of Free Human Oligosaccharides.

Authors:  Boram Bae; Haeun Kim; Hyerin Park; Young Jun Koh; Sung-Jin Bae; Ki-Tae Ha
Journal:  Biomolecules       Date:  2021-05-21
  10 in total

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