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2004 | 51 | 1 | 121-127
Article title

Stereochemistry of insect kinin tetrazole analogues and their diuretic activity in crickets.

Content
Title variants
Languages of publication
EN
Abstracts
EN
Insect kinin analogues of the sequence Phe-Phe-ψ[CN4]-Ala-Trp-Gly-NH2 containing (L-Phe2,L-Ala3) and (L-Phe2,D-Ala3) stereochemical variants of the tetrazole moiety, a mimic of the type VI β-turn, demonstrate significant agonist and partial antagonist activity, respectively, in a cricket diuretic bioassay. A comparison of the solution conformations of these two stereochemical variants indicates a structural basis for their divergent bioactivities. The (D-Phe2,D-Ala3) stereochemical variant was synthesized and found to demonstrate significant agonist activity. The results further define stereochemical requirements for the diuretic activity of insect kinins in crickets and provide valuable information for the design of biostable analogues capable of disrupting digestive and diuretic processes in pest insects.
Publisher

Year
Volume
51
Issue
1
Pages
121-127
Physical description
Dates
published
2004
received
2003-10-31
revised
2004-01-23
accepted
2004-02-03
Contributors
  • Areawide Pest Management Research Unit, Southern Plains Agricultural Research Center, ARS, U.S. Department of Agriculture, College Station, TX, U.S.A.
  • School of Biological and Chemical Sciences, Birkbeck College, London, U.K.
  • Areawide Pest Management Research Unit, Southern Plains Agricultural Research Center, ARS, U.S. Department of Agriculture, College Station, TX, U.S.A.
  • Department of Chemistry, Texas A&M University, College Station, TX, U.S.A
  • Institute of Organic Chemistry, Technical University of Lodz, Łódź, Poland
References
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Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.bwnjournal-article-abpv51i1p121kz
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