Literature DB >> 19719157

Synthesis of stapled beta3-peptides through ring-closing metathesis.

Ylva E Bergman1, Mark P Del Borgo, Romila D Gopalan, Sania Jalal, Sharon E Unabia, Marisa Ciampini, Daniel J Clayton, Jordan M Fletcher, Roger J Mulder, Jacqueline A Wilce, Marie-Isabel Aguilar, Patrick Perlmutter.   

Abstract

The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with O-allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.

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Year:  2009        PMID: 19719157     DOI: 10.1021/ol901803d

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


  6 in total

1.  Bridged beta(3)-peptide inhibitors of p53-hDM2 complexation: correlation between affinity and cell permeability.

Authors:  Arjel D Bautista; Jacob S Appelbaum; Cody J Craig; Julien Michel; Alanna Schepartz
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

2.  Transition of Nano-Architectures Through Self-Assembly of Lipidated β3-Tripeptide Foldamers.

Authors:  Nathan Habila; Ketav Kulkarni; Tzong-Hsien Lee; Zahraa S Al-Garawi; Louise C Serpell; Marie-Isabel Aguilar; Mark P Del Borgo
Journal:  Front Chem       Date:  2020-03-31       Impact factor: 5.221

Review 3.  Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes.

Authors:  Marta Pelay-Gimeno; Adrian Glas; Oliver Koch; Tom N Grossmann
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-26       Impact factor: 15.336

4.  Chiral tether-mediated stabilization and helix-sense control of complementary metallo-double helices.

Authors:  Miki Horie; Naoki Ousaka; Daisuke Taura; Eiji Yashima
Journal:  Chem Sci       Date:  2014-09-10       Impact factor: 9.825

Review 5.  Structural and pharmacological effects of ring-closing metathesis in peptides.

Authors:  Øyvind Jacobsen; Jo Klaveness; Pål Rongved
Journal:  Molecules       Date:  2010-09-21       Impact factor: 4.411

6.  Z-Selective olefin metathesis on peptides: investigation of side-chain influence, preorganization, and guidelines in substrate selection.

Authors:  Shane L Mangold; Daniel J O'Leary; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2014-08-20       Impact factor: 15.419

  6 in total

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