A study of the - isomerization preference of -alkylated peptides containing phosphorus in the side chain and backbone
The current work provides a study on the cis - trans isomerization behaviour of N -alkylated peptides decorated with phosphonate ester groups. A Ugi four-component reaction was chosen for the synthesis of N -alkylated peptides, where almost only the cis isomer was detected when the phosphonate ester...
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Published in | New journal of chemistry Vol. 43; no. 32; pp. 1284 - 12813 |
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Main Authors | , , , , , , , , , |
Format | Journal Article |
Published |
12.08.2019
|
Online Access | Get full text |
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Summary: | The current work provides a study on the
cis
-
trans
isomerization behaviour of
N
-alkylated peptides decorated with phosphonate ester groups. A Ugi four-component reaction was chosen for the synthesis of
N
-alkylated peptides, where almost only the
cis
isomer was detected when the phosphonate ester group was incorporated as an amine component in the side chain. However, the phosphonate ester group inserted in the backbone, as an isocyanide component, leads preferably to the
trans
isomer of this kind of peptides. The diverse behaviour of
cis
-
trans
isomerization has been explained
via
spectroscopic nuclear magnetic resonance analysis and computational calculations.
The current work provides a study on the
cis
-
trans
isomerization behaviour of
N
-alkylated peptides decorated with phosphonate ester groups. |
---|---|
Bibliography: | 10.1039/c9nj02234a Electronic supplementary information (ESI) available. See DOI |
ISSN: | 1144-0546 1369-9261 |
DOI: | 10.1039/c9nj02234a |