1997
DOI: 10.1002/(sici)1097-0282(199709)42:3<373::aid-bip9>3.0.co;2-j
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Role of two consecutive α,β-dehydrophenylalanines in peptide structure: Crystal and molecular structure of Boc-Leu-ΔPhe-ΔPhe-Ala-Phe-NHMe

Abstract: An Nα‐protected model pentapeptide containing two consecutive ΔPhe residues, Boc‐Leu‐ΔPhe‐ΔPhe‐Ala‐Phe‐NHMe, has been synthesized by solution methods and fully characterized. 1H‐nmr studies provided evidence for the occurrence of a significant population of a conformer having three consecutive, intramolecularly H‐bonded β‐bends in solution. The solid state structure has been determined by x‐ray diffraction methods. The crystals grown from aqueous methanol are orthorhombic, space group P212121, a = 11.503(2), b… Show more

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Cited by 14 publications
(5 citation statements)
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“…In BocAlaΔPheΔPheNHMe, Tuzi et al31 found two independent molecules in the crystallographic unit; a right‐handed and a left‐handed 3 10 ‐helix. In most peptides containing two consecutive ΔPhe residues such as BocValΔPheΔPheValOMe or BocLeuΔPheΔPheAlaPheNHMe, a well‐aligned right‐handed 3 10 ‐helical conformation is stabilized 79–82. It can be speculated that consecutive ΔPhe‐containing peptides possessing bulky L residues favor the formation of a right‐handed 3 10 ‐helix.…”
Section: Conformational Studiesmentioning
confidence: 99%
“…In BocAlaΔPheΔPheNHMe, Tuzi et al31 found two independent molecules in the crystallographic unit; a right‐handed and a left‐handed 3 10 ‐helix. In most peptides containing two consecutive ΔPhe residues such as BocValΔPheΔPheValOMe or BocLeuΔPheΔPheAlaPheNHMe, a well‐aligned right‐handed 3 10 ‐helical conformation is stabilized 79–82. It can be speculated that consecutive ΔPhe‐containing peptides possessing bulky L residues favor the formation of a right‐handed 3 10 ‐helix.…”
Section: Conformational Studiesmentioning
confidence: 99%
“…It may the 01-CS bond [e2, = -58.6", OZ2 = 65.0"~ e2, = 177.2~1. Circular dichroism studies were carried out to probe the (17,27,28).…”
Section: Resultsmentioning
confidence: 99%
“…Privileged solution conformations of Δ Z Phe‐based peptides were satisfactorily determined by NMR analysis . Short peptides containing Δ Z Phe residues were generally shown to fold into conformations that may be perturbed by the H‐bonding capabilities of the solvent.…”
Section: Cαβ‐didehydro‐α‐amino Acid‐containing Peptidesmentioning
confidence: 99%
“…As in the case of the aforementioned Aib peptides discussed, many ΔPhe‐containing linear peptides are highly crystalline materials. This property allows X‐ray diffraction analyses to be performed . Almost all of them are characterized by the Δ Z Phe configurational isomer.…”
Section: Cαβ‐didehydro‐α‐amino Acid‐containing Peptidesmentioning
confidence: 99%