Synthesis of achiral alpha,alpha-disubstituted beta-alanines, and their use in construction of libraries of beta-peptide conjugates of N-2-alkyl-1,2,3,4-tetrahydroisoquinolines on a solid support



: Heinonen P, Virta P, Lonnberg H

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

: 1999

Tetrahedron

TETRAHEDRON

: TETRAHEDRON

: 55

: 24

: 7613

: 7624

: 12

: 0040-4020

DOI: https://doi.org/10.1016/S0040-4020(99)00378-6


Six achiral N-phthaloyl protected alpha,alpha-disubstituted beta-amino acids were synthesized, and used to construct a 96 compound library of 1,2,3,4-tetrahydroisaquinoline conjugates of beta-peptides on a solid support. The library synthesis consisted of attachment of an appropriately 5-O-tethered 1,2,3,4-tetrahydroisoquinoline via the N-2 atom to a vinyl sulfonyl support, elongation of the deprotected 5-O-tether by repeated peptide coupling, quaternarization of N-2 with alkylamines and release of the beta-peptide conjugate into solution with triethylamine. (C) 1999 Elsevier Science Ltd. All rights reserved.



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