Abstract
The solution-phase synthesis of the marine sponge stylopeptide 1 (2), cyclo-(Leu-Ile-Phe-Ser-Pro-Ile-Pro), was conveniently accomplished using N-terminal Fmoc- and C-terminal tert-butyl ester protection with tert-butyl ether side-chain blocking for serine. Peptide bond formation for each step except for the final cyclization was effected with diethyl phosphorocyanidate to give the linear heptapeptide in 19% yield. Both TBTU (4) or BOP-Cl (5) were used to cyclize the heptapeptide and resulted in 67% and 13% yields of stylopeptide 1 (2), respectively. Peptide 2 was obtained in 11% overall yield based on the TBTU cyclization procedure. The general approach represents a useful improvement in the synthesis of such cyclic peptides. The synthetic stylopeptide 1 (2) proved to be identical with the natural product.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
