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Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids
University of Sheffield, Uk.
Medivir AB, Sweden; F-star Biotechnology Ltd, UK.
Medivir AB, Sweden.
Medivir AB, Sweden; FOI Swedish Defence Research Agency, Sweden.
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2019 (English)In: ACS Omega, ISSN 2470-1343, Vol. 4, no 6, p. 10854-10865Article in journal (Refereed) Published
Abstract [en]

A range of enantiomerically pure protected side-chain-fluorinated amino acids has been prepared (13 examples) by treatment of protected amino acids containing unsaturated side chains with a combination of Fe(III)/NaBH4 and Selectfluor. The modification of the conditions by replacement of Selectfluor with NaN3 allowed the preparation of side-chain azido-substituted amino acids (five examples), which upon catalytic hydrogenation gave the corresponding amines, isolated as lactams (four examples). Radical hydration of the unsaturated side chains leading to side-chain-hydroxylated protected amino acids has also been demonstrated.

Place, publisher, year, edition, pages
American Chemical Society , 2019. Vol. 4, no 6, p. 10854-10865
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Natural Sciences
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URN: urn:nbn:se:ri:diva-42781DOI: 10.1021/acsomega.9b01509Scopus ID: 2-s2.0-85067654283OAI: oai:DiVA.org:ri-42781DiVA, id: diva2:1384779
Available from: 2020-01-10 Created: 2020-01-10 Last updated: 2020-01-10Bibliographically approved

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