Evidence map›Paper›PMID 40881114›Full record

ArticlePrecision chemistry2023

An Unusual Acceleration of Amination Reactivity by the Proximal Ester Groups in Catechol Diesters: An Efficient Way for Peptide Synthesis.

An Wu, Hirotaka Ikeda, Hisashi Yamamoto

Abstract read
In one paragraph

Article in Precision chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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1 · What the graph read from it

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4 · The record

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5 · Who and what money

Authors and funding

3 authors.

An WuPeptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan.ORCID https://orcid.org/0000-0001-7179-5590
Hirotaka IkedaMaterials Science Department, MOLSIS Inc., 3-19-9, Hatchobori, Chuo-ku, Tokyo 104-0032, Japan.
Hisashi YamamotoPeptide Research Center, Chubu University, 1200 Matsumoto-cho, Kasugai, Aichi 487-8501, Japan.ORCID https://orcid.org/0000-0001-5384-9698

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Peptide bond formation has drawn more and more attention due to its importance in medicinal chemistry and drug discovery. Using active esters to construct peptide bonds is an indispensable strategy in this field. We herein report a fast and efficient amination reaction to synthesize peptides from catechol diesters. Catechol monoesters are good active esters in peptide synthesis due to the anchimeric assistance effect. In previously reported work, the amination reaction was inactivated if the 2-hydroxyl group in the catechol esters was functionalized. However, we found an unusual acceleration of the amination reactivity when the 2-hydroxyl group was functionalized as an ester group. The reaction can be complete in 2-3 min in some cases. This acceleration was found through experimental studies to not result from the anchimeric assistance effect. We proposed a π*-π* interaction pathway between the two proximal ester groups. Some computational studies were made to support this assumption.

Indexed as

aminationcatechol diesterspeptide synthesisproximal ester groupsπ*−π* interaction

Identifiers

PMID40881114
PMCPMC12382259

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.