N-alpha-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15110%2F18%3A73590811" target="_blank" >RIV/61989592:15110/18:73590811 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/18:73590811

Result on the web

<a href="http://dx.doi.org/10.1039/c8ob01485j" target="_blank" >http://dx.doi.org/10.1039/c8ob01485j</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c8ob01485j" target="_blank" >10.1039/c8ob01485j</a>

Result language

angličtina

Original language name

N-alpha-Amino acid containing privileged structures: design, synthesis and use in solid-phase peptide synthesis

Original language description

Fmoc-protected N-amino acid containing heterocyclic privileged structures, O-(1-methyl-5-oxo-2,5-dihydro-1H-pyrrol-3-yl)-L-serine and O-((S)-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)-L-serine, were synthesized on the solid phase from simple commercially available building blocks under mild conditions. The amino acid side-chain is composed of tetramic acid, a natural product derived privileged structure. The key transformation was the formation of cyclic enol ethers via nonclassical Wittig olefinations of the esters. Solid-phase synthesis represents a method of choice, particularly for the synthesis of peptides. This route is compatible with traditional Merrifield solid-phase peptide synthesis (SPPS), as documented on the preparation of the pentapeptide Leu-enkephalin amide H-Tyr-Gly-Gly-Phe-Leu-NH2 with Phe or Tyr replaced by a novel amino acid.

Czech name

—

Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2018

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

ORGANIC &amp; BIOMOLECULAR CHEMISTRY

ISSN

1477-0520

e-ISSN

—

Volume of the periodical

16

Issue of the periodical within the volume

29

Country of publishing house

GB - UNITED KINGDOM

Number of pages

4

Pages from-to

5359-5362

UT code for WoS article

000439945800018

EID of the result in the Scopus database

2-s2.0-85050738226