Literature DB >> 15040728

Synthesis of novel S-neoglycopeptides from glycosylthiomethyl derivatives.

Xiangming Zhu1, Kandasamy Pachamuthu, Richard R Schmidt.   

Abstract

Reaction of glycosylthiomethyl azides with amino acid and peptide derivatives containing aspartate and glutamate thio acids gave the corresponding glycosylthiomethyl amides in excellent yields. Another type of neoglycopeptides was obtained via reaction of glycosylthiomethyl bromide with cysteine and homocysteine containing peptide derivatives, thus affording the corresponding S-(glycosylthiomethyl) peptides.

Entities:  

Year:  2004        PMID: 15040728     DOI: 10.1021/ol036186z

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  7 in total

1.  Sigmatropic rearrangements as tools for amino acid and peptide modification: application of the allylic sulfur ylide rearrangement to the preparation of neoglycoconjugates and other conjugates.

Authors:  David Crich; Yekui Zou; Franck Brebion
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

Review 2.  Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2003-2004.

Authors:  David J Harvey
Journal:  Mass Spectrom Rev       Date:  2009 Mar-Apr       Impact factor: 10.946

3.  Reaction of thioacids with isocyanates and isothiocyanates: a convenient amide ligation process.

Authors:  David Crich; Kaname Sasaki
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005

4.  Allylic selenosulfide rearrangement: a method for chemical ligation to cysteine and other thiols.

Authors:  David Crich; Venkataramanan Krishnamurthy; Thomas K Hutton
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

5.  Thiomaleic anhydride: a convenient building block for the synthesis of alpha-substituted gamma- and delta-lactones through free-radical addition, nucleophilic ring opening, and subsequent thiocarboxylate manipulation.

Authors:  David Crich; Md Yeajur Rahaman
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides.

Authors:  David Crich; Fan Yang
Journal:  J Org Chem       Date:  2008-08-27       Impact factor: 4.354

7.  An expeditious and efficient bromomethylation of thiols: enabling bromomethyl sulfides as useful building blocks.

Authors:  Carolina Silva-Cuevas; Ehecatl Paleo; David F León-Rayo; J Armando Lujan-Montelongo
Journal:  RSC Adv       Date:  2018-07-10       Impact factor: 4.036

  7 in total

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