Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides.

The Journal of Organic Chemistry
David Crich, Fan Yang

Abstract

Two series of neoglycosyl donors are prepared on the basis of connection of an allylic disulfide motif to the anomeric center via a simple O-glycosyl linkage or N-glycosyl amide unit. Conjugation of both sets of donors to cysteine in peptides is demonstrated through classical disulfide exchange followed by the phosphine-mediated desulfurative allylic rearrangement resulting in neoglycopeptides characterized by a simple thioether spacer. The conjugation reaction functions in the absence of protecting groups on both the neoglycosyl donor and peptide in aqueous media at room temperature.

References

Jun 1, 1973·The Journal of Organic Chemistry·R E Hackler, T W Balko
Jan 1, 1980·Advances in Carbohydrate Chemistry and Biochemistry·C P Stowell, V C Lee
Jun 24, 2000·Bioorganic & Medicinal Chemistry Letters·Y OhnishiY Ichikawa
Aug 10, 2000·Organic Letters·L Jobron, G Hummel
Feb 14, 2002·Chemical Reviews·Benjamin G Davis
Apr 27, 2002·The Journal of Organic Chemistry·Spencer Knapp, David S Myers
Dec 3, 2003·Organic & Biomolecular Chemistry·David P GamblinBenjamin G Davis
Feb 24, 2004·Chemistry : a European Journal·Xiangming Zhu, Richard R Schmidt
Mar 11, 2004·Chemical Communications : Chem Comm·Francesco Peri, Francesco Nicotra
Mar 26, 2004·Organic Letters·Xiangming ZhuRichard R Schmidt
Jul 2, 2005·Angewandte Chemie·Desiree A ThayerChi-Huey Wong
Sep 28, 2005·Chemistry : a European Journal·Katie J DooresBenjamin G Davis
Jan 4, 2006·The Journal of Organic Chemistry·Srinivas Hotha, Sudhir Kashyap
Jan 13, 2006·Chemical Reviews·Kandasamy Pachamuthu, Richard R Schmidt
Feb 24, 2006·Journal of the American Chemical Society·David CrichThomas K Hutton
Mar 23, 2006·Journal of the American Chemical Society·Yoshiyasu IchikawaMinoru Isobe
Apr 6, 2006·Journal of the American Chemical Society·Vincent LadmiralDavid M Haddleton
Apr 19, 2006·Nature Chemical Biology·James C PaulsonBrian E Collins
May 6, 2006·Glycobiology·Therese BuskasGeert-Jan Boons
May 26, 2007·Journal of the American Chemical Society·Yu-Ying YangChi-Huey Wong
Aug 23, 2007·Journal of the American Chemical Society·Isaac J KraussSamuel J Danishefsky
Jan 31, 2008·Journal of the American Chemical Society·Sharmishtha SamantarayRajendra P Roy
Feb 16, 2008·Angewandte Chemie·Gonçalo J L BernardesBenjamin G Davis
Mar 14, 2008·Organic Letters·Larry E OvermanHelen F Sneddon
May 3, 2008·Chemical Reviews·Heather E Murrey, Linda C Hsieh-Wilson
Jul 18, 2008·The Journal of Organic Chemistry·Zhe LiLei Liu

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Citations

Nov 17, 2009·The Journal of Organic Chemistry·David CrichMaheswaran Karatholuvhu
May 11, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Venkata R KrishnamurthyElliot L Chaikof
Jun 27, 2009·Chemical Communications : Chem Comm·Justin M ChalkerBenjamin G Davis
Mar 24, 2016·Chemical Communications : Chem Comm·Eric G Gharakhanian, Timothy J Deming
Oct 16, 2018·Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry·Seiji Sakamoto, Itaru Hamachi
May 1, 2010·Biomolecular Concepts·Carmen Jiménez-CastellsRicardo Gutiérrez-Gallego
Jan 11, 2019·Chemical Science·David MontoirSamir Messaoudi
Feb 25, 2009·Chemistry, an Asian Journal·Justin M ChalkerBenjamin G Davis
Jul 25, 2013·Chemical Communications : Chem Comm·Alexandre NovoaNicolas Winssinger

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