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Literature DB >> 25506740

Access to large cyclic peptides by a one-pot two-peptide segment ligation/cyclization process.

Emmanuelle Boll¹, Jean-Philippe Ebran, Hervé Drobecq, Ouafâa El-Mahdi, Laurent Raibaut, Nathalie Ollivier, Oleg Melnyk.

Abstract

The use of the N-acetoacetyl protecting group for N-terminal cysteine residue enabled creation of an efficient and mild one-pot native chemical ligation/SEA ligation sequence giving access to large cyclic peptides.

Entities: Chemical

Mesh：

Substances：

Year: 2014 PMID： 25506740 DOI： 10.1021/ol503359w

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

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Cited

7 in total

1. Total chemical synthesis, refolding, and crystallographic structure of fully active immunophilin calstabin 2 (FKBP12.6).

Authors: Marine Bacchi; Magali Jullian; Serena Sirigu; Benjamin Fould; Tiphaine Huet; Lisa Bruyand; Mathias Antoine; Laurent Vuillard; Luisa Ronga; Leonard M G Chavas; Olivier Nosjean; Gilles Ferry; Karine Puget; Jean A Boutin
Journal: Protein Sci Date: 2016-10-13 Impact factor: 6.725

2. Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid-hydroxylamine (KAHA) ligation.

Authors: Florian Rohrbacher; André Zwicky; Jeffrey W Bode
Journal: Chem Sci Date: 2017-04-24 Impact factor: 9.825

7. A simple and traceless solid phase method simplifies the assembly of large peptides and the access to challenging proteins.

Authors: N Ollivier; R Desmet; H Drobecq; A Blanpain; E Boll; B Leclercq; A Mougel; J Vicogne; O Melnyk
Journal: Chem Sci Date: 2017-05-30 Impact factor: 9.825

7 in total

Access to large cyclic peptides by a one-pot two-peptide segment ligation/cyclization process.

1. Total chemical synthesis, refolding, and crystallographic structure of fully active immunophilin calstabin 2 (FKBP12.6).

2. Chemical synthesis of a homoserine-mutant of the antibacterial, head-to-tail cyclized protein AS-48 by α-ketoacid-hydroxylamine (KAHA) ligation.

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

4. Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation.

5. Redox-Controlled Chemical Protein Synthesis: Sundry Shades of Latency.

6. Accelerated microfluidic native chemical ligation at difficult amino acids toward cyclic peptides.

7. A simple and traceless solid phase method simplifies the assembly of large peptides and the access to challenging proteins.