α-Glycosylation by D-glucosamine-derived donors: synthesis of heparosan and heparin analogues that interact with mycobacterial heparin-binding hemagglutinin

Journal of the American Chemical Society
Medel Manuel L ZuluetaShang-Cheng Hung

Abstract

Numerous biomolecules possess α-D-glucosamine as structural component. However, chemical glycosylations aimed at this backbone are usually not easily attained without generating the unwanted β-isomer. We report herein a versatile approach in affording full α-stereoselectivity built upon a carefully selected set of orthogonal protecting groups on a D-glucosaminyl donor. The excellent stereoselectivity provided by the protecting group combination was found independent of leaving groups and activators. With the trichloroacetimidate as the optimum donor leaving group, core skeletons of glycosylphosphatidyl inositol anchors, heparosan, heparan sulfate, and heparin were efficiently assembled. The orthogonal protecting groups were successfully manipulated to further carry out the total syntheses of heparosan tri- and pentasaccharides and heparin di-, tetra-, hexa-, and octasaccharide analogues. Using the heparin analogues, heparin-binding hemagglutinin, a virulence factor of Mycobacterium tuberculosis, was found to bind at least six sugar units with the interaction notably being entropically driven.

References

Jul 1, 1976·Angewandte Chemie·H PaulsenW Stenzel
Jan 1, 1988·Annual Review of Biochemistry·M A Ferguson, A F Williams
Mar 28, 2001·Science·C R Bertozzi, L L Kiessling
Sep 6, 2001·Journal of the American Chemical Society·H M NguyenD Y Gin
Mar 28, 1996·Chemical Reviews·Raymond A. Dwek
Sep 5, 2002·Journal of the American Chemical Society·Paul T NyffelerChi-Huey Wong
Dec 20, 2002·Angewandte Chemie·Ishan Capila, Robert J Linhardt
May 9, 2003·Natural Product Reports·Ken-ichi Kimura, Timothy D H Bugg
Jun 13, 2003·Journal of Medicinal Chemistry·Robert J Linhardt
Jun 26, 2003·Journal of the American Chemical Society·Ning ShangguanLawrence J Williams
Jan 15, 2004·Journal of the American Chemical Society·Jinq-Chyi LeeShang-Cheng Hung
Jun 17, 2004·Angewandte Chemie·Maurice Petitou, Constant A A van Boeckel
Nov 24, 2004·Current Opinion in Chemical Biology·Brian E Collins, James C Paulson
Jan 22, 2005·Journal of Medicinal Chemistry·Ulf LindahlBenito Casu
Feb 11, 2005·Chemical Reviews·Sophie Magnet, John S Blanchard
Jul 14, 2005·Chemical Reviews·John M Whitelock, Renato V Iozzo
Jul 26, 2005·Chemistry & Biology·Christian Noti, Peter H Seeberger
Nov 29, 2005·Biochemical and Biophysical Research Communications·Eva MuñozRobert J Linhardt
Aug 31, 2006·Journal of the American Chemical Society·Zhitao Li, Jeffrey C Gildersleeve
Nov 28, 2006·Carbohydrate Research·Aileen F G Bongat, Alexei V Demchenko
Apr 20, 2007·Nature·Cheng-Chung WangShang-Cheng Hung
Apr 21, 2007·Chemistry : a European Journal·Alexander AdibekianPeter H Seeberger
Apr 27, 2007·Nature·Joseph R BishopJeffrey D Esko
Oct 5, 2007·Journal of the American Chemical Society·Tülay Polat, Chi-Huey Wong
Jan 15, 2008·Nature Protocols·Cheng-Chung WangShang-Cheng Hung
Apr 22, 2008·FEMS Microbiology Reviews·Bin LiuLei Wang
Sep 6, 2008·Microbiology and Molecular Biology Reviews : MMBR·Gerald L NewtonRobert C Fahey
Dec 24, 2008·Chemistry : a European Journal·Pratap S Patil, Shang-Cheng Hung
Apr 24, 2009·Natural Product Reports·Sherket PetersonJian Liu

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Citations

Nov 18, 2015·The Journal of Organic Chemistry·Steven B DulaneyXuefei Huang
Nov 5, 2013·Current Opinion in Chemical Biology·Medel Manuel L ZuluetaShang-Cheng Hung
Apr 20, 2016·Proceedings of the National Academy of Sciences of the United States of America·Wenguang G LiangWei-Jen Tang
Jun 10, 2016·Journal of the American Chemical Society·Katie L StewartDavid A Middleton
Jul 14, 2016·Chemical Reviews·Marco MendeStefan Bräse
Sep 28, 2016·Chemical Reviews·Renata Marcia de FigueiredoJean-Marc Campagne
May 16, 2017·The Journal of Organic Chemistry·Jun-Hao WanJian-Song Sun
Apr 11, 2015·Organic & Biomolecular Chemistry·Baolin WuTiehai Li
Mar 10, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Brooke L FarrugiaJohn M Whitelock
Nov 8, 2018·Organic & Biomolecular Chemistry·Qi Qi HeVito Ferro
May 8, 2019·Nature Chemical Biology·Kazuma SakamotoKenji Kadomatsu
Jul 22, 2014·Angewandte Chemie·Cheng-Hsiu ChangShang-Cheng Hung
Mar 21, 2020·Organic & Biomolecular Chemistry·Dancan K NjeriJustin R Ragains
Oct 26, 2016·ChemistryOpen·Rituparna Das, Balaram Mukhopadhyay
Sep 11, 2012·Angewandte Chemie·Bo YangXuefei Huang
Apr 16, 2015·Angewandte Chemie·Jiakun Li, Biao Yu
Feb 28, 2013·Chemical Communications : Chem Comm·Medel Manuel L ZuluetaShang-Cheng Hung
Mar 12, 2021·Chemical Communications : Chem Comm·Prashant JainRaghavendra Kikkeri
Mar 17, 2019·Carbohydrate Research·Xin LiuJian-Song Sun
Jul 17, 2019·ACS Infectious Diseases·Daniel F EarleyMark von Itzstein
Apr 22, 2015·Chemical Reviews·Tobias Gylling FrihedChristian Marcus Pedersen
Jun 22, 2013·The Journal of Organic Chemistry·Nerea GuedesNiels-Christian Reichardt
Jun 6, 2018·Chemical Reviews·Suvarn S KulkarniShang-Cheng Hung
Jun 29, 2018·Chemical Reviews·Matteo PanzaAlexei V Demchenko
May 1, 2015·Organic Letters·Satsawat VisansirikulAlexei V Demchenko
Dec 18, 2012·Organic Letters·Steen U HansenJohn M Gardiner
Feb 23, 2020·Journal of the American Chemical Society·Li-Ting ChiuShang-Cheng Hung
May 8, 2020·The Journal of Organic Chemistry·Liming WangJeroen D C Codée

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