2002
DOI: 10.1002/psc.394
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Conformational solution studies of [Sar7]desamino‐ and [MeAla7]desamino‐ vasopressin analogues using NMR spectroscopy

Abstract: Solution structures of two analogues of vasopressin with an amino acid sequence of c[Mpa1-Tyr2-Phe3-Gln4-Asn5-Cys6]-Xaa7-Arg8-Gly9-NH2 (Xaa = Sar [I] or MeAla [II]) were established using ROE and the 3J(HNH alpha) couplings. Each of the peptides was found to exist in two stable isomers, pertaining to the cis or trans status of the Cys6-Xaa7 peptide bond, thus giving rise to four study objects. Two methods for studies of the conformational properties of the structures were compared. In the first, the algorithm … Show more

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Cited by 8 publications
(8 citation statements)
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“…The conformational preference of neurohypophyseal peptide hormones and their analogues has been investigated by various techniques, such as laser Raman spectroscopy and CD [40], NMR spectroscopy in different solvents [21,[42][43][44][45][46][47][48][49]], x-ray crystallography [50][51][52] and other physicochemical methods [35,53]. It is generally believed that the cyclic part contains a β-or γ -turn structure, whereas the acyclic tail is very flexible.…”
Section: Discussionmentioning
confidence: 99%
See 1 more Smart Citation
“…The conformational preference of neurohypophyseal peptide hormones and their analogues has been investigated by various techniques, such as laser Raman spectroscopy and CD [40], NMR spectroscopy in different solvents [21,[42][43][44][45][46][47][48][49]], x-ray crystallography [50][51][52] and other physicochemical methods [35,53]. It is generally believed that the cyclic part contains a β-or γ -turn structure, whereas the acyclic tail is very flexible.…”
Section: Discussionmentioning
confidence: 99%
“…Furthermore, a β-turn at positions 4 and 5 was detected in a trifluoroethanol solution of desmopressin [43]. An inverse γ -turn centred at Gln 4 was detected in analogues of oxytocin and vasopressin [37,[47][48][49]51]. Both in aqueous solution and at a pH similar to physiological conditions, desmopressin was found to contain a stable inverse γ -turn centred around Gln 4 [45].…”
Section: Discussionmentioning
confidence: 99%
“…Also a distorted type II β ‐turn has been found in the noncyclic moiety of the peptide. Recently reported conformational studies of two vasopressin analogs in water, [MeAla 7 ]dAVP and [Sar 7 ]dAVP, revealed also β ‐turns in the Tyr 2 ‐Asn 2 region (47). Computer‐aided simulations with the analogs of [Cpp 1 ]AVP, [OCA 1 ]AVP and [SCA 1 ]AVP (48) showed also existence of the β ‐turns at positions Phe 3 ‐Glu 4 and Glu 4 ‐Asn 5 .…”
Section: Discussionmentioning
confidence: 99%
“…However, in those containing either proline residues or N‐methylated amino acids, the cis/trans isomerism of the peptide Aaa‐Pro and Aaa‐Me‐Aaa bond occurs fairly frequently. For instance, substitution of the MeAla or Sar in position 7 of vasopressin (47) or oxytocin (50) results in appearance of the cis/trans isomerism of the peptide bond preceding the modified amino acid moiety.…”
Section: Discussionmentioning
confidence: 99%
“…At the same time, the C-terminal tail modulates binding affinities via a few intermolecular contacts [66] . Indeed, SAR studies of VP revealed that modification or replacement of Pro 7 in VP can affect V 1a /V 2 receptor selectivity [67] , [68] .…”
Section: Discussionmentioning
confidence: 99%