Amino acid derivatives of β-cyclodextrin

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

doi:10.1021/jo951396d

Amino acid derivatives of β-cyclodextrin

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

Chemistry

Research output: Contribution to journal › Article › peer-review

260 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 language	English (US)
Pages (from-to)	903-908
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	61
Issue number	3
DOIs	https://doi.org/10.1021/jo951396d
State	Published - Feb 9 1996

ASJC Scopus subject areas

Organic Chemistry

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title = "Amino acid derivatives of β-cyclodextrin",

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.",

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T1 - Amino acid derivatives of β-cyclodextrin

AU - Ashton, Peter R.

AU - Königer, Rainer

AU - Stoddart, J. Fraser

AU - Alker, David

AU - Harding, Valerie D.

PY - 1996/2/9

Y1 - 1996/2/9

N2 - 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.

AB - 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.

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Amino acid derivatives of β-cyclodextrin

Abstract

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