Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides-Reference-Cited by-同舟云学术

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Methyl to trifluoromethyl substitution as a strategy to increase the membrane permeability of short peptides

Published:2021 Issue:43 Volume:19 Page:9386-9389
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Ono Takahiro¹^ORCID,Aikawa Kohsuke¹,Okazoe Takashi¹²,Morimoto Jumpei¹^ORCID,Sando Shinsuke¹³^ORCID

Affiliation:

1. Department of Chemistry & Biotechnology, Graduate School of Engineering, The University of Tokyo, Bunkyo-ku, Tokyo 113-8656, Japan

2. Material Integration Laboratories, Yokohama Technical Center, AGC Inc., Yokohama 230-0045, Japan

3. Department of Bioengineering, Graduate School of Engineering, The University of Tokyo, Bunkyo-ku, Tokyo 113-8656, Japan

Abstract

CH3 to CF3 substitution on a side chain of proteiogenic amino acids increases the membrane permeability of peptides.

Funder

AGC

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/OB/D1OB01565F

Reference23 articles.

1. Macrocyclic Peptides as Drug Candidates: Recent Progress and Remaining Challenges

2. Improving Oral Bioavailability of Peptides by Multiple N-Methylation: Somatostatin Analogues

3. On-resin N-methylation of cyclic peptides for discovery of orally bioavailable scaffolds

4. Rational design and synthesis of an orally bioavailable peptide guided by NMR amide temperature coefficients

5. Connecting Hydrophobic Surfaces in Cyclic Peptides Increases Membrane Permeability

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