Literature DB >> 26075704

Synthesis of Unprotected Linear or Cyclic O-Acyl Isopeptides in Water Using Bis(2-sulfanylethyl)amido Peptide Ligation.

Rémi Desmet1, Mindaugas Pauzuolis1, Emmanuelle Boll1, Hervé Drobecq1, Laurent Raibaut1, Oleg Melnyk1.   

Abstract

SEA ligation proceeds chemoselectively at pH 3, i.e., at a pH where the O-acyl isopeptides are protected by protonation. This property was used for synthesizing unprotected O-acyl isopeptides in water, starting from peptide segments which are easily accessible by the Fmoc SPPS.

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Year:  2015        PMID: 26075704     DOI: 10.1021/acs.orglett.5b01614

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


  2 in total

Review 1.  Recent advances in the synthesis of C-terminally modified peptides.

Authors:  Christine A Arbour; Lawrence G Mendoza; Jennifer L Stockdill
Journal:  Org Biomol Chem       Date:  2020-09-30       Impact factor: 3.890

2.  Accelerating chemoselective peptide bond formation using bis(2-selenylethyl)amido peptide selenoester surrogates.

Authors:  Laurent Raibaut; Marine Cargoët; Nathalie Ollivier; Yun Min Chang; Hervé Drobecq; Emmanuelle Boll; Rémi Desmet; Jean-Christophe M Monbaliu; Oleg Melnyk
Journal:  Chem Sci       Date:  2016-01-11       Impact factor: 9.825

  2 in total

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