TY - JOUR
T1 - Synthesis of the Dolastatin 3 Isomer cyclo-[L-Pro-L-Leu-L-Val-(-R,S)-(gln)Thz-(gly)Thz]
AU - Pettit, George
AU - Holzapfel, Cedric W.
PY - 1986/1/1
Y1 - 1986/1/1
N2 - With application of mixed carbonic anhydride and dicyclohexylcarbodiimide-N-hydroxysuccinimide peptide bond forming methods culminating in a 2,4,5-trichlorophenol active ester promoted cyclization reaction, synthesis (cf., Scheme I) of cyclo-[L-Pro-L-Leu-L-Val-(R,S)-(gln)Thz-(gly)Thz] was completed. Comparison of this cyclic peptide with the Indian Ocean sea hare cell growth inhibitory constituent dolastatin 3 clearly showed that the natural peptide possesses a closely related structure. The high resolution (400 MHz) 1H NMR and 13C NMR spectra of the synthetic peptides were evaluated in detail and suggested that dolastatin 3 may contain (R)-(gln)Thz and/or a modified Pro-Leu-Val sequence.
AB - With application of mixed carbonic anhydride and dicyclohexylcarbodiimide-N-hydroxysuccinimide peptide bond forming methods culminating in a 2,4,5-trichlorophenol active ester promoted cyclization reaction, synthesis (cf., Scheme I) of cyclo-[L-Pro-L-Leu-L-Val-(R,S)-(gln)Thz-(gly)Thz] was completed. Comparison of this cyclic peptide with the Indian Ocean sea hare cell growth inhibitory constituent dolastatin 3 clearly showed that the natural peptide possesses a closely related structure. The high resolution (400 MHz) 1H NMR and 13C NMR spectra of the synthetic peptides were evaluated in detail and suggested that dolastatin 3 may contain (R)-(gln)Thz and/or a modified Pro-Leu-Val sequence.
UR - http://www.scopus.com/inward/record.url?scp=0022857996&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0022857996&partnerID=8YFLogxK
U2 - 10.1021/jo00374a017
DO - 10.1021/jo00374a017
M3 - Article
AN - SCOPUS:0022857996
SN - 0022-3263
VL - 51
SP - 4580
EP - 4585
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 24
ER -