Synthesis of protected derivatives of 3-pyrrolylalanine

Creators: Beecher, Jody E.; Tirrell, David A.

Abstract

Protected derivatives of 3-pyrrolylalanine (3-PA) have been synthesized starting with N-tri(isopropyl)silylpyrrole. Following formylation and Boc protection, treatment with (±)-N-(benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester provided a fully protected dehydro-3-pyrrolylalanine. Reduction of the double bond and removal of the methyl ester groups yielded 3-PA protected at the α- and pyrrole nitrogens. 3-PA is only transiently stable following N-deprotection.

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© 1998 Elsevier. Received 27 February 1998; revised 24 March 1998; accepted 1 April 1998. This work was supported by a grant from the Polymers and Genetics Programs of the National Science Foundation. NMR spectra were recorded in the University of Massachusetts NMR Laboratory, which is supported by the NSF Materials Research Laboratory at the University. Jody Beecher thanks the National Institutes of Health for financial support of her postdoctoral research.

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Synthesis of protected derivatives of 3-pyrrolylalanine

Abstract

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