Conformational investigation of alpha,beta-dehydropeptides. XIII. Conformational properties of N-acetyl-alpha,beta-dehydrovaline N',N'-dimethylamide. | Zendy

Dawid Siodłak | Zendy; Barbara Rzeszotarska | Zendy; Małgorzata A. Broda | Zendy; A.E. Kozioł | Zendy; E. Kołodziejczyk | Zendy

Open Access

Conformational investigation of alpha,beta-dehydropeptides. XIII. Conformational properties of N-acetyl-alpha,beta-dehydrovaline N',N'-dimethylamide.

Author(s) -

Dawid Siodłak,

Barbara Rzeszotarska,

Małgorzata A. Broda,

A.E. Kozioł,

E. Kołodziejczyk

Publication year - 2004

Publication title -

acta biochimica polonica

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.452

H-Index - 78

eISSN - 1734-154X

pISSN - 0001-527X

DOI - 10.18388/abp.2004_3606

Subject(s) - beta (programming language) , chemistry , amide , crystallography , stereochemistry , ab initio , molecule , alpha (finance) , residue (chemistry) , crystal structure , mathematics , construct validity , organic chemistry , computer science , programming language , statistics , biochemistry , psychometrics

The crystal structure of Ac-DeltaVal-NMe(2) (DeltaVal = alpha,beta-dehydrovaline) was determined by X-ray crystallography. The found angles phi = -60 degrees and psi = 125 degrees correspond exactly to the respective values of the (i + 1)th residue in idealised beta-turn II/VIa. Ab initio/DFT studies revealed that the molecule adopts the angle psi restricted only to about |130 degrees | and very readily attains the angle phi = about -50 degrees. This is in line with its solid-state conformation. Taken together, these data suggest that the DeltaVal residue combined with a C-terminal tertiary amide is a good candidate at the (i + 1)th position in a type II/VIa beta-turn.

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