Model Dipeptides Incorporating the trans Cyclohexane Analogues of Phenylalanine: Further Evidence of the Relationship Between Side‐Chain Orientation and β‐Turn Type.

descriptionPublicationkeyboard_double_arrow_right Article , Other literature type 01 Nov 2005 Spain English Publisher:WileyJournal:ChemInform, volume 37 (issn: 0931-7597, eissn: 1522-2667,

Copyright policy )

Authors: Lasa, Marta; Jiménez, Ana I.; Zurbano, María M.; Cativiela, Carlos;

doi: 10.1002/chin.200605197 , 10.1016/j.tetlet.2005.09.155

handle: 10261/271996

Model Dipeptides Incorporating the trans Cyclohexane Analogues of Phenylalanine: Further Evidence of the Relationship Between Side‐Chain Orientation and β‐Turn Type.

- Summary
- Metrics

Abstract

In order to study the influence of the side-chain orientation on the peptide backbone conformation we have synthesised the model dipeptides t-BuCO-l-Pro-(1S,2R)-c6Phe-NHMe and t-BuCO-l-Pro-(1R,2S)-c6Phe-NHMe, incorporating each enantiomer of the trans cyclohexane analogue of phenylalanine (trans-1-amino-2-phenylcyclohexanecarboxylic acid). The orientation of the aromatic side-chain determines the β-turn type accommodated by these peptides to the point that the (1S,2R)-c6Phe derivative retains the type I β-turn in the crystalline state, in contrast to the behaviour exhibited by the natural counterpart t-BuCO-l-Pro-l-Phe-NHMe.

Financial support from Ministerio de Educación y Ciencia—FEDER (project PPQ2004-5358) and Diputación General de Aragón is gratefully acknowledged.

Peer reviewed

Country

Spain

Related Organizations

Impact byBIP!

	selected citations These citations are derived from selected sources. This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	9
	popularity This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.	Average
	influence This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).	Average
	impulse This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.	Average