Synthesis of achiral alpha,alpha-bis(aminomethyl)-beta-alanines and their use in the preparation of branched beta-peptide conjugates of N-2-alkyl-1,2,3,4-tetrahydroisoquinolines on solid support



: Heinonen P, Rosenberg J, Lonnberg H

Publisher: WILEY-V C H VERLAG GMBH

: 2000

European Journal of Organic Chemistry

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

: EUR J ORG CHEM

: 21

: 3647

: 3652

: 6

: 1434-193X


Three achiral branching units 1-3 derived from alpha,alpha -bis(aminomethyl)-beta -alanine were synthesized and evaluated in the construction of branched and sterically compact beta -peptide conjugates on a solid support. Several peptide conjugates bearing an N-alkylated 1,2,3,4-tetrahydroisoquinoline moiety were prepared to demonstrate the applicability of the branching units in a solid phase peptide synthesis. The most useful building block 3 incorporated Boc-protected aminomethyl side chains at the alpha -carbon of N-phthaloyl-beta -alanine.



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