Amino acid derivatives of β-cyclodextrin

Peter R. Ashton, Rainer Königer, J. Fraser Stoddart, David Alker, Valerie D. Harding

Research output: Contribution to journalArticlepeer-review

240 Scopus citations

Abstract

The syntheses of the heptaamino acid-substituted β-cyclodextrins per-6-[(phenylalanyl)amino]-β-cyclodextrin (6), per-6-cysteinyl-β-cyclodextrin (7), as well as the per-2,3-dimethyl-per-6-cysteinyl-β-cyclodextrin (12) are described. The amino acids were coupled to the primary face of the β-cyclodextrin torus using the backbone carboxylic acid functionality of phenylalanine and the side chain thiol group of cysteine. In the case of the heptacysteinyl derivatives, polyzwitterionic compounds were obtained and shown to be highly water soluble.

Original languageEnglish (US)
Pages (from-to)903-908
Number of pages6
JournalJournal of Organic Chemistry
Volume61
Issue number3
DOIs
StatePublished - Feb 9 1996

ASJC Scopus subject areas

  • Organic Chemistry

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