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

Kemisk Institut

14 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Organic & Biomolecular Chemistry
Sider (fra-til)	1173-1180
Antal sider	7
ISSN	1477-0520
DOI	https://doi.org/10.1039/b917145b
Status	Udgivet - 11 jan. 2010

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10.1039/b917145b

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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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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

C2 - 20165810

SN - 1477-0520

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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