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Letters in Peptide Science

, Volume 4, Issue 4–6, pp 441–445 | Cite as

Synthesis and applications of cyclopeptides and depsipeptides

  • John S. Davies
  • Joanne Howe
  • Janitha Jayatilake
  • Tony Riley
Article
  • 166 Downloads

Summary

A solid phase protocol has been devised for the synthesis of linear precursors to cyclic depsipeptide analogues of dolastatin D.t-Butyldimethylsilyl groups were used for hydroxy group protection, with deprotection being carried out byt-butyl ammonium fluoride. HATU and PyBrop were successful in coupling highly hindered residues and in depside bond formation. Cyclic peptide analogues, cyclo[Arg-Gly-Asp-d-Phe-Lys(or Tyr)] have been synthesised and modified for use as carrier molecules for the transport of radio isotopes (111In and125I) into blood platelets as prototypes for medical imaging.

Keywords

Solid phase Depside synthesis t-Butyldimethylsilyl protection HATU/PyBrop couplings Dolastatin D analogues Cyclic RGD pentapeptides DTPA derivatisation 

Abbreviations

PyBrop

bromotrispyrrolidinophosphonium hexafluorophosphate

Hiv

hydroxyisovaleric acid

PhLac

phenyllactic acid

TFA

trifluoroacetic acid

HATU

O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

TBTU

2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate

HOBt

N-hydroxybenzotriazole

MeCN

acetonitrile

DIEA

diisopropylethyl amine

DMSO

dimethylsulfoxide

DMF

N,N-dimethylformamide

THF

tetrahydrofuran

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Copyright information

© Kluwer Academic Publishers 1997

Authors and Affiliations

  • John S. Davies
    • 1
  • Joanne Howe
    • 1
  • Janitha Jayatilake
    • 1
  • Tony Riley
    • 2
  1. 1.Chemistry DepartmentUniversity of WalesSwanseaU.K.
  2. 2.Amersham International plcAmershamU.K.

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