Source:http://linkedlifedata.com/resource/pubmed/id/20580135
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
9
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pubmed:dateCreated |
2010-8-9
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pubmed:abstractText |
In this paper we use NMR spectroscopy and molecular modeling to examine four vasopressin analogues substituted with bulky 3,3'-diphenylalanine (Dpa) enantiomers: [Mpa(1),Dpa(2),Val(4),D-Arg(8)]VP (I), [Mpa(1),D-Dpa(2),Val(4),D-Arg(8)]VP (II), [D-Dpa(2),D-Arg(8)]VP (III) and [Mpa(1),D-Dpa(2)]AVP (IV). All the peptides exhibit a strong and prolonged antidiuretic activity. Additionally, analogues II, III and IV display antiuterotonic activity and analogue II is also a weak V(1a) receptor blocker. The conformational analysis has shown that beta-turns at positions 2,3 and/or 3,4 are characteristic of OT antagonists. In turn, the beta-turn in the Cys(6)-Gly(9) fragment seems to be crucial for enhancement of the antidiuretic activity. The high accessibility of aromatic side chains at positions 2 and 3 plays a crucial role in antagonist-receptor binding. Moreover, orientation of the Phe(3) side chain is claimed to be important for V(1a) receptor affinity.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical | |
pubmed:status |
MEDLINE
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pubmed:month |
Sep
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pubmed:issn |
1768-3254
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pubmed:author | |
pubmed:copyrightInfo |
2010 Elsevier Masson SAS. All rights reserved.
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pubmed:issnType |
Electronic
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pubmed:volume |
45
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
4065-73
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pubmed:meshHeading |
pubmed-meshheading:20580135-Amino Acid Sequence,
pubmed-meshheading:20580135-Arginine Vasopressin,
pubmed-meshheading:20580135-Magnetic Resonance Spectroscopy,
pubmed-meshheading:20580135-Models, Molecular,
pubmed-meshheading:20580135-Phenylalanine,
pubmed-meshheading:20580135-Protein Conformation,
pubmed-meshheading:20580135-Stereoisomerism
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pubmed:year |
2010
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pubmed:articleTitle |
Influence of bulky 3,3'-diphenylalanine enantiomers replacing position 2 of AVP analogues on their conformations: NMR and molecular modeling studies.
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pubmed:affiliation |
Faculty of Chemistry, University of Gda?sk, Sobieskiego 18, 80-952 Gda?sk, Poland. milka@chem.univ.gda.pl
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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