Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

Michael Pittelkow; Jeremy K. M. Sanders; Mark G. Simpson; Stephen P. Watson

doi:10.1039/b917145b

Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

Michael Pittelkow, Jeremy K. M. Sanders, Mark G. Simpson, Stephen P. Watson

Department of Chemistry

14 Citations (Scopus)

Abstract

We describe an efficient and general strategy for the synthesis of dimethyl acetal functionalised steroidal hydrazides based on the cholic acid skeleton with the aim of using these compounds as building blocks for dynamic combinatorial chemistry. Deprotection of the acetal protected building blocks with TFA leads to formation of libraries containing macrocyclic N-acyl hydrazone oligomers. The isolation of several of these, and their characterisation using NMR is described. The effects on the equilibrium library distribution by varying the substituents at C-7 and C-12, extending the side-chain with glycine, and inverting the configuration at C-3 are discussed. Finally, we report the exchange properties of these macrocycles and demonstrate new examples of proof-reading and self-sorting in dynamic combinatorial libraries.

Original language	English
Journal	Organic & Biomolecular Chemistry
Pages (from-to)	1173-1180
Number of pages	7
ISSN	1477-0520
DOIs	https://doi.org/10.1039/b917145b
Publication status	Published - 11 Jan 2010

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title = "Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries",

abstract = "We describe an efficient and general strategy for the synthesis of dimethyl acetal functionalised steroidal hydrazides based on the cholic acid skeleton with the aim of using these compounds as building blocks for dynamic combinatorial chemistry. Deprotection of the acetal protected building blocks with TFA leads to formation of libraries containing macrocyclic N-acyl hydrazone oligomers. The isolation of several of these, and their characterisation using NMR is described. The effects on the equilibrium library distribution by varying the substituents at C-7 and C-12, extending the side-chain with glycine, and inverting the configuration at C-3 are discussed. Finally, we report the exchange properties of these macrocycles and demonstrate new examples of proof-reading and self-sorting in dynamic combinatorial libraries.",

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T1 - Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

AU - Pittelkow, Michael

AU - Sanders, Jeremy K. M.

AU - Simpson, Mark G.

AU - Watson, Stephen P.

PY - 2010/1/11

Y1 - 2010/1/11

N2 - We describe an efficient and general strategy for the synthesis of dimethyl acetal functionalised steroidal hydrazides based on the cholic acid skeleton with the aim of using these compounds as building blocks for dynamic combinatorial chemistry. Deprotection of the acetal protected building blocks with TFA leads to formation of libraries containing macrocyclic N-acyl hydrazone oligomers. The isolation of several of these, and their characterisation using NMR is described. The effects on the equilibrium library distribution by varying the substituents at C-7 and C-12, extending the side-chain with glycine, and inverting the configuration at C-3 are discussed. Finally, we report the exchange properties of these macrocycles and demonstrate new examples of proof-reading and self-sorting in dynamic combinatorial libraries.

AB - We describe an efficient and general strategy for the synthesis of dimethyl acetal functionalised steroidal hydrazides based on the cholic acid skeleton with the aim of using these compounds as building blocks for dynamic combinatorial chemistry. Deprotection of the acetal protected building blocks with TFA leads to formation of libraries containing macrocyclic N-acyl hydrazone oligomers. The isolation of several of these, and their characterisation using NMR is described. The effects on the equilibrium library distribution by varying the substituents at C-7 and C-12, extending the side-chain with glycine, and inverting the configuration at C-3 are discussed. Finally, we report the exchange properties of these macrocycles and demonstrate new examples of proof-reading and self-sorting in dynamic combinatorial libraries.

U2 - 10.1039/b917145b

DO - 10.1039/b917145b

M3 - Journal article

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SP - 1173

EP - 1180

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

ER -

Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

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