Conformational studies of <i>N</i>‐acetyl‐<i>N</i>′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. II. Conformational energy calculations and comparison with experimental results

Abe, Akihiro; Yamazaki, Toshimasa

doi:10.1002/bip.360270608

Biopolymers

1988

DOI: 10.1002/bip.360270608

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Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. II. Conformational energy calculations and comparison with experimental results

Akihiro Abe

Toshimasa Yamazaki

Abstract: SynopsisConformational analyses on a series of dipeptides CH,-with side chains such as R = CH2CH3,.CH,CH,CH,, and CH(CH,), are described.

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Cited by 4 publications

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Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by ¹H‐nmr spectroscopy

Yamazaki

Abe

1988

Biopolymers

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SynopsisThe 'H-nmr studies were extensively carried out to elucidate preferred conformations of dipeptides CH,C*O-X-NHCH,, with X = Abu, oval, and Val in various solvents. The vicinal 'H--'H coupling constants for the NH-CnH moiety and those around the C"-Cp bond in the articulated side chain provided the information regarding the average conformation of these molecules. The results indicate that transformation of skeletal conformations takes place in solution among conformers having similar dihedral angles, 8,,-,.,, in the Karplus expression.

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Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by ¹H‐nmr spectroscopy

Yamazaki

Abe

1988

Biopolymers

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Conformational studies of stereoisomeric 14‐membered cyclic enkephalin analogues containing 1‐naphthyialanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity

et al. 1991

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In order to study structure-activity relationships of enkephalin-related analogues, we report the biological activity and conformational analysis of four 14-membered cyclic enkephalin analogues with beta-(1-naphthyl) alanine in place of phenylalanine at the fourth position, Tyr-c[D-A2bu-Gly-(L and D)-beta Nal(1)-(L and D)-Leu]. The L-beta Nal(1)-containing analogues display higher activity at both the mu and delta receptors than the corresponding analogues with the L-Phe residue. In contrast to the linear enkephalins, the cyclic analogues with the D-beta Nal(1) residue are also active at the mu receptor since the relative spatial arrangement of functional groups required for biological activity is achieved by the constrained nature of the cyclic molecules. A comparison of the findings from the conformational analysis and biological assays establishes that relatively extended structures, in which the two aromatic side chains are oriented in opposite directions with a approximately 14 A separation, is required for activity at the mu receptor. On the other hand, folded conformations with nearly parallel orientations and a close proximity (less than 10A) of the aromatic rings of the Tyr and beta Nal(1) residues are required for activity at the delta receptor. It should be noted that the overall structures and thus the biological profiles of the 14-membered cyclic enkephalin analogues are strongly dependent on the conformation of the second residue. The folded conformations with parallel orientation of the two aromatic side chains of Tyr-c[D-A2bu-Gly-L-beta Nal(1)-D-Leu] is stabilized by an interaction between the Tyr phenolic OH proton and beta Nal(1) C*O groups. This analogue, which shows the highest activity at both the mu and delta receptors among the four stereoisomers studied, displays an increase of the fraction of the side-chain chi 1 = t conformer for the beta Nal(1) residue. It is concluded that the incorporation of the D-Leu residue at the fifth position increases the relative fraction of the folded conformations with parallel orientation of the aromatic side chains, and hence enhances activity at the delta receptor as compared to the corresponding L-Leu containing analogue.

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Vibrational circular dichroism studies of molecular conformation and association of dipeptides

Miyazawa

Kyogoku

Sugeta

1994

Spectrochimica Acta Part A: Molecular Spectroscopy

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Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. II. Conformational energy calculations and comparison with experimental results

Abstract: SynopsisConformational analyses on a series of dipeptides CH,-with side chains such as R = CH2CH3,.CH,CH,CH,, and CH(CH,), are described.

Cited by 4 publications

References 25 publications

Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by ¹H‐nmr spectroscopy

Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by ¹H‐nmr spectroscopy

Conformational studies of stereoisomeric 14‐membered cyclic enkephalin analogues containing 1‐naphthyialanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity

Vibrational circular dichroism studies of molecular conformation and association of dipeptides

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Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. II. Conformational energy calculations and comparison with experimental results

Abstract: SynopsisConformational analyses on a series of dipeptides CH,-with side chains such as R = CH2CH3,.CH,CH,CH,, and CH(CH,), are described.

Cited by 4 publications

References 25 publications

Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by 1H‐nmr spectroscopy

Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by 1H‐nmr spectroscopy

Conformational studies of stereoisomeric 14‐membered cyclic enkephalin analogues containing 1‐naphthyialanine at the fourth position: Chirality effect of leucine at the fifth position on biological activity and receptor selectivity

Vibrational circular dichroism studies of molecular conformation and association of dipeptides

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Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by ¹H‐nmr spectroscopy

Conformational studies of N‐acetyl‐N′‐methylamide derivatives of α‐aminobutyric acid, norvaline, and valine. I. Preferred conformations in solution as studied by ¹H‐nmr spectroscopy