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Trifluoroacetyl as an orthogonal protecting group for guanidines

Trifluoroacetyl as an orthogonal protecting group for guanidines
Trifluoroacetyl as an orthogonal protecting group for guanidines
The trifluoroacetyl moiety has been used as a new protecting group for guanidine functionality. The protecting group is easily cleaved under mild basic conditions and is complementary to the Boc, Cbz, and Ddpe protecting groups. The protecting group can be applied to peptide synthesis in solution as well as on a solid phase as it is orthogonal to a Boc and Cbz strategy and semiorthogonal to an Fmoc strategy.
molecular tweezers, carboxylic-acids, receptor, complexation, recognition, libraries, design, water
0022-3263
9416-9422
Bartoli, S.
7954394a-dd77-4757-8fc3-fdaaab56b5cf
Jensen, K. B.
2f8e42a5-d90b-41d5-8043-68577624027f
Kilburn, J. D.
c02957da-baca-4138-961a-a85170d11dd8
Bartoli, S.
7954394a-dd77-4757-8fc3-fdaaab56b5cf
Jensen, K. B.
2f8e42a5-d90b-41d5-8043-68577624027f
Kilburn, J. D.
c02957da-baca-4138-961a-a85170d11dd8

Bartoli, S., Jensen, K. B. and Kilburn, J. D. (2003) Trifluoroacetyl as an orthogonal protecting group for guanidines. Journal of Organic Chemistry, 68 (24), 9416-9422. (doi:10.1021/jo0348874).

Record type: Article

Abstract

The trifluoroacetyl moiety has been used as a new protecting group for guanidine functionality. The protecting group is easily cleaved under mild basic conditions and is complementary to the Boc, Cbz, and Ddpe protecting groups. The protecting group can be applied to peptide synthesis in solution as well as on a solid phase as it is orthogonal to a Boc and Cbz strategy and semiorthogonal to an Fmoc strategy.

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More information

Published date: 28 November 2003
Keywords: molecular tweezers, carboxylic-acids, receptor, complexation, recognition, libraries, design, water
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Identifiers

Local EPrints ID: 19893
URI: http://eprints.soton.ac.uk/id/eprint/19893
DOI: doi:10.1021/jo0348874
ISSN: 0022-3263
PURE UUID: 28a3a5a3-75f2-47bb-9f2a-662ac0f0f5ba

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Date deposited: 20 Feb 2006
Last modified: 15 Mar 2024 06:20

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Contributors

Author: S. Bartoli
Author: K. B. Jensen
Author: J. D. Kilburn

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