2004年4月
Stereoselective terminal functionalization of small peptides for catalytic asymmetric synthesis of unnatural peptides
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
- ,
- ,
- 巻
- 101
- 号
- 16
- 開始ページ
- 5824
- 終了ページ
- 5829
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1073/pnas.0307725101
- 出版者・発行元
- NATL ACAD SCIENCES
The asymmetric phase-transfer catalytic alkylation of peptides has been achieved by the use of designed C-2-symmetric chiral quaternary ammonium bromide 1 as catalyst. Excellent stereoselectivities were uniformly observed in the alkylation with a variety of alkyl halides and the efficiency of the transmission of stereochemical information was not affected by the side-chain structure of the preexisting amino acid residues. This method also enables an asymmetric construction of noncoded alpha,alpha-dialkyl-alpha-amino acid residues at the peptide terminal. Since this chirality can be efficiently transferred to the adjacent amino acid moiety, our approach provides a general procedure not only for the highly stereoselective terminal functionalization of peptides but also for the sequential asymmetric construction of unnatural oligopeptides, which should play a vital role in the peptide-based drug discovery process.
- リンク情報
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- DOI
- https://doi.org/10.1073/pnas.0307725101
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/15079083
- PubMed Central
- https://www.ncbi.nlm.nih.gov/pmc/articles/PMC395993
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000220978000027&DestApp=WOS_CPL
- URL
- http://europepmc.org/abstract/med/15079083
- URL
- http://orcid.org/0000-0002-0309-9507
- ID情報
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- DOI : 10.1073/pnas.0307725101
- ISSN : 0027-8424
- ORCIDのPut Code : 48496291
- PubMed ID : 15079083
- PubMed Central 記事ID : PMC395993
- Web of Science ID : WOS:000220978000027