Collect. Czech. Chem. Commun.
2000, 65, 407-424
https://doi.org/10.1135/cccc20000407
1-Deamino-1(15)-carba and -Dicarba Analogues of Endothelin-1
Jan Hlaváček*, Renáta Marcová, Miloš Buděšínský and Jiřina Slaninová
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
Abstract
Sulfanyl-methylene and ethylene bridges were inserted into the molecule of endothelin-1 (ET-1) as other possible isosteric replacements of its outer disulfide linkage. The [1-deamino-1-carba]ET-1, [1-deamino-15-carba]ET-1 and [1-deamino-1,15-dicarba]ET-1 were synthesized either by a fragment condensation of protected cyclic pentadecapeptides with carboxy-terminal hexapeptides of the endothelin-1 sequence or by step-wise coupling on polymer support of the entire henicosapeptide sequences from carboxy-terminus. The analogues were devoid of uterotonic activity in comparison with the parent ET-1.
Keywords: Peptides; Solid phase synthesis; Step-wise procedure; Fragment condensation; Endothelin; Disulfide isosters; Uterotonic activity.
References: 37 live references.
