Synthesis of sequential polypeptides containing L‐azetidine‐2‐carboxylic acid residues

The synthesis and characterization of a series of sequential polypeptides with the repeating sequences Aze‐Pro‐Aze, Pro‐Aze‐Pro, Pro‐Aze‐Gly, Aze‐Pro‐Gly, Ala‐Aze‐Gly, Aze‐Ala‐Gly, and Pro‐Pro‐Gly are reported. The polymers were prepared by the active ester method, using the p‐nitrophenyl, pentachlorophenyl, and N‐hydroxysuccinimide esters as the polymerizable tripeptide derivatives. Except for poly(Ala‐Aze‐Gly) obtained via the N‐hydroxysuccinimide ester, all polymers were isolated in good yields and have weight‐average molecular weights in the range 10,000–30,000. The molecular weights have been determined by applying the calibrated gel chromatography system described by Fairweather et al. [J. Chromatogr. (1972) 67, 157] and by viscometry. All di‐ and tripeptide intermediates were chemically and optically pure.

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