Stabilization of Neutral NH2-R-COOH Form of the Antihypertensive Peptides L-Valyl-L-Prolyl-L-Proline and L-Isoleucyl-L-Prolyl-L-Proline

被引：4

作者：

Kolev, Tsonko ^{[1
,2
]}

Koleva, Bojidarka B. ^{[3
]}

Stoineva, Ivanka ^{[1
]}

Jakimova, Boryana ^{[1
]}

Tchorbanov, Bojidar ^{[1
]}

机构：

[1] Bulgarian Acad Sci, Inst Organ Chem, BU-1113 Sofia, Bulgaria

[2] Paisij Hilendarski Univ Plovdiv, Dept Organ Chem, BG-4000 Plovdiv, Bulgaria

[3] Sofia Univ St Kl Ohridsky, Fac Chem, Sofia 1164, Bulgaria

来源：

PROTEIN AND PEPTIDE LETTERS | 2009年 / 16卷 / 02期

关键词：

Tripeptide; H-Val-Pro-Pro-OH; H-Ile-Pro-Pro-OH; angiotensin-I converting enzyme; VALIDATION; GLYCINE;

D O I：

10.2174/092986609787316315

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Spectroscopic and structural elucidation of the peptides (L)-Valyl-(L)-Prolyl-(L)-Proline (1) and (L)-Isoleucyl-(L)-Prolyl-(L)-Proline (2) are reported on the basis of experimental linear-polarized IR-spectroscopy in solid-state, H-1-NMR data and DFT. Curiously, the experimental data shown that both peptides stabilized in solution and in solid-state neutral H2N-RCOOH form. Conformational analysis made, shown two strong intramolecular NH2...O=C-N-(Amide) and O=C-OH...NH2 hydrogen bonds with lengths of 2.979 angstrom and 2.475 angstrom in (1) and 2.599 angstrom and 2.507 angstrom in (2) respectively. The presence of the Pro-Pro fold resulted to strong steric effect leading to the stabilization of free COOH and NH2 groups. The E-rel values of zwitterion form are significant higher than the neutral forms with a difference of 1.2 and 0.9 kJ/mol. The manner of interaction of the peptides with angiotensin-I converting enzyme is proposed.

引用

页码：112 / 115

页数：4

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