Cyclization of disulfide-containing peptides in solid-phase synthesis.
作者： FERNANDO ALBERICIO , ROBERT P. HAMMER , CARLOS GARCÍA-ECHEVERRÍA , M. ANTÒNIA MOLINS , JANE L. CHANG
DOI: 10.1111/J.1399-3011.1991.TB00755.X
关键词:
摘要: Disulfide-containing peptides may be obtained in good yields and purities when oxidations are carried out on peptide chains anchored to polymeric supports used for solid-phase synthesis. Such approaches take advantage of the pseudo-dilution phenomenon which favors intramolecular processes. A variety procedures have been demonstrated using related model Ac-Cys-Pro-D Val-Cys-NH2 Ac-Pen-Pro-D (which both readily assume a type II beta-turn conformation that becomes stabilized by 14-membered disulfide-containing ring), oxytocin (conformationally mobile 20-membered disulfide ring). Both Boc Fmoc were N alpha-amino protection, beta-thiols cysteine or penicillamine blocked S-acetamidomethyl (Acm), S-9-fluorenylmethyl (Fm), S-trityl (Trt), compatible anchoring linkages included HF-labile 4-methylbenzhydrylamide (MBHA), TFA-labile tris (alkoxy)benzylamide (PAL), photolabile o-nitrobenzylamide (Nonb). Assemblies linear sequences proceeded smoothly, polymer-supported ways either directly after deblocking resin-bound dithiol. Chains released from support without substantial damage bridges, overall as high 60-90%.
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