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Literature DB >> 14586119

Effect of alpha,alpha-dialkyl amino acids on the protease resistance of peptides.

Hiroshi Yamaguchi¹, Hiroaki Kodama, Satoshi Osada, Fumio Kato, Masood Jelokhani-Niaraki, Michio Kondo.

Abstract

A tryptic [EC 3.4.21.4] digestion assay of 2-aminoisobutyric acid (Aib)-containing peptides was carried out to investigate the effect of alpha,alpha-dialkyl amino acid residues on the protease resistance. The introduction of Aib residues to the P1' positions exhibited a 19-fold higher protease resistance than the peptide with Aib residues introduced to the P2 position or the non-Aib peptide. The peptide having Aib residues introduced to the P1' and P2 positions resulted in complete resistance.

Entities: Chemical Gene

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Year: 2003 PMID： 14586119 DOI： 10.1271/bbb.67.2269

Source DB: PubMed Journal: Biosci Biotechnol Biochem ISSN： 0916-8451 Impact factor: 2.043

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Cited

12 in total

1. Pronase E-Based Generation of Fluorescent Peptide Fragments: Tracking Intracellular Peptide Fate in Single Cells.

Authors: Emilie R Mainz; Nicholas C Dobes; Nancy L Allbritton
Journal: Anal Chem Date: 2015-07-24 Impact factor: 6.986

2. Targeting diverse protein-protein interaction interfaces with α/β-peptides derived from the Z-domain scaffold.

Authors: James W Checco; Dale F Kreitler; Nicole C Thomas; David G Belair; Nicholas J Rettko; William L Murphy; Katrina T Forest; Samuel H Gellman
Journal: Proc Natl Acad Sci U S A Date: 2015-03-30 Impact factor: 11.205

3. Iterative Nonproteinogenic Residue Incorporation Yields α/β-Peptides with a Helix-Loop-Helix Tertiary Structure and High Affinity for VEGF.

Authors: James W Checco; Samuel H Gellman
Journal: Chembiochem Date: 2017-01-09 Impact factor: 3.164

Effect of alpha,alpha-dialkyl amino acids on the protease resistance of peptides.

1. Pronase E-Based Generation of Fluorescent Peptide Fragments: Tracking Intracellular Peptide Fate in Single Cells.

2. Targeting diverse protein-protein interaction interfaces with α/β-peptides derived from the Z-domain scaffold.

3. Iterative Nonproteinogenic Residue Incorporation Yields α/β-Peptides with a Helix-Loop-Helix Tertiary Structure and High Affinity for VEGF.

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8. In silico molecular engineering for a targeted replacement in a tumor-homing peptide.

9. Peptides displayed as high density brush polymers resist proteolysis and retain bioactivity.

10. Secondary structures and cell-penetrating abilities of arginine-rich peptide foldamers.