Abstract
Introduction The octapeptide sequence Leu1-Met2-Tyr3-Pro4-Thr5-Tyr6-Leu7-Lys8-OH (1) is reported to be a receptor binding inhibitor of vasoactive intestinal peptide. The anticancer activity of octapeptide 1 in combination with other neuropeptide analogs has been reported [1]. Here we report the peptidomimetic analogs of octapeptide 1 by incorporating furanoid sugar amino acids 2-4. We replaced either Tyr-Pro (analogs 5 and 5a) or Pro-Thr (analogs 6, 6a and 7) in the sequence by furanoid sugar amino acids as depicted in the following figure. In independent studies in the laboratory, the truncated pentapeptide sequence, Met-Pro-Thr-Tyr-Leu-OH, derived from octapeptide 1, was also found to be as active as 1. We also synthesized analogs to this pentapeptide by replacing its Pro-Thr dipeptide segment with sugar amino acids 2 and 3 to get the peptides 8 and 9, respectively.
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