Conformations of cis‐ and trans‐2, 3‐methanomethionine stereoisomers in the tripeptide mimic system Ac{cyclo‐M}NHiPr
- 1 March 1997
- journal article
- Published by Wiley in Chemical Biology & Drug Design
- Vol. 49 (3) , 201-209
- https://doi.org/10.1111/j.1399-3011.1997.tb00879.x
Abstract
Quenched molecular dynamics (QMD) was used to simulate low-energy conformers of the tripeptide mimics Ac¿cyclo-Met¿NHiPr, where the 2.3-methanomethionine is the cis-derivative (2R,3S)-cyclo-Met and the trans-derivative (2R,3R)-cyclo-Met. Variations of the favored omicron, upsilon values. and differences between the simulated preferred conformations for the two structures, were rationalized and discussed. Physical data for the cis-derivative (NMR, CD and FT-IR) gave no conclusive evidence for any preferred conformation. However for the trans-derivative, Ac¿(2R,3R)-cyclo-Met¿NHiPr, the physical data suggests that a conformer with partial helical structure is favored. This work provides details of how the rigidly constrained side chain and cyclopropane of 2,3-methanoamino acids can be used to manipulate phi, psi values in a logical fashion.Keywords
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