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

• Authors: Ronald J Nachman , Geoffrey M Coast , Krzysztof Kaczmarek , Howard J Williams , Janusz Zabrocki
• 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.

Keywords

EN

constrained insect kinin analogue; tetrazole; diuresis; cis-peptide bond; β-turn mimetic

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2004
• Volume: 51
• Issue: 1
• Pages: 121-127

Dates

published

2004

received

2003-10-31

revised

2004-01-23

accepted

2004-02-03

Contributors

author

Ronald J Nachman

• Areawide Pest Management Research Unit, Southern Plains Agricultural Research Center, ARS, U.S. Department of Agriculture, College Station, TX, U.S.A.

author

Geoffrey M Coast

• School of Biological and Chemical Sciences, Birkbeck College, London, U.K.

author

Krzysztof Kaczmarek

• Areawide Pest Management Research Unit, Southern Plains Agricultural Research Center, ARS, U.S. Department of Agriculture, College Station, TX, U.S.A.

author

Howard J Williams

• Department of Chemistry, Texas A&M University, College Station, TX, U.S.A

author

Janusz Zabrocki

• Institute of Organic Chemistry, Technical University of Lodz, Łódź, Poland

References

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