Chemistry of Natural Compounds

, Volume 25, Issue 4, pp 475–484 | Cite as

Synthesis of C-terminal fragments of bombesin and their analogues

  • I. L. Kuranova
  • S. I. Churkina
  • V. L. Dyudmirova
  • E. B. Filonova
  • F. M. Ibatullin
  • F. K. Mutulis
  • I. P. Sekatsis
  • V. D. Grigor'eva


With the aim of structural-functional studies in the bombesin series, a number of bombesin fragments and analogues have been synthesized. The synthesis was performed by the carbodiimide method and by the activated-ester method. Fragments with the sequences 7–14, 8–14, and 9–14 were obtained by 4+4, 3+4, and 2+4 schemes and a pentapeptide with the sequence 9–13 by a 3 + 2 scheme. Acetylation of the octapeptide BN(7–14) was carried out by the action of acetic anhydride in pyridine. Analogues of the C-terminal nonapeptide of bombesin [DPhe7]BN(6–14) and [Pro6, Gly7, DAla11]BN(6–14) were synthesized by fragment condensation using the 5 + 4 scheme. The individuality of the compounds obtained was confirmed by their chromatographic behavior on plates coated with silica gel, and by the results of amino acid analysis, high-voltage electrophoresis, and high-performance liquid chromatography, and their structures were confirmed by the results of high-resolution1H NMR spectroscopy (360 MHz). In experiments on rabbits, in a dose of 1 µg with central administration the full hypothermic effect of bombesin was shown by the preparation [AcGln7]BN(7–14), while the preparation [DPhe7]BN(6–14) and [Pro6,Gly7,DAla11]BN(6–14) possessed only a slight effect (∼1% of the activity of bombesin).


Dipeptide Bombesin Preparative HPLC Vasoactive Peptide Main Spot 


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Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • I. L. Kuranova
  • S. I. Churkina
  • V. L. Dyudmirova
  • E. B. Filonova
  • F. M. Ibatullin
  • F. K. Mutulis
  • I. P. Sekatsis
  • V. D. Grigor'eva

There are no affiliations available

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