A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

Steven A. Kates; Nuria A. Solé; Charles R. Johnson; Derek Hudson; George Barany; Fernando Albericio

doi:10.1016/0040-4039(93)85003-F

A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

Steven A. Kates, Nuria A. Solé, Charles R. Johnson, Derek Hudson, George Barany, Fernando Albericio

Chemistry (Twin Cities)

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

240 Scopus citations

Abstract

Head-to-tail cyclic peptides are made by an efficient three-dimensional orthogonal solid-phase strategy (Fmoc/tBu/allyl), featuring side-chain anchoring to PAC or PAL supports, selective palladium (O)-catalyzed allyl removal, and resin-bound cyclization mediated by BOP/HOBt/DIEA.

Original language	English (US)
Pages (from-to)	1549-1552
Number of pages	4
Journal	Tetrahedron Letters
Volume	34
Issue number	10
DOIs	https://doi.org/10.1016/0040-4039(93)85003-F
State	Published - Mar 5 1993

Keywords

allyl esters
cyclic peptides
orthogonal protection
pseudo-dilution
solid-phase synthesis

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T1 - A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

AU - Kates, Steven A.

AU - Solé, Nuria A.

AU - Johnson, Charles R.

AU - Hudson, Derek

AU - Barany, George

AU - Albericio, Fernando

PY - 1993/3/5

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AB - Head-to-tail cyclic peptides are made by an efficient three-dimensional orthogonal solid-phase strategy (Fmoc/tBu/allyl), featuring side-chain anchoring to PAC or PAL supports, selective palladium (O)-catalyzed allyl removal, and resin-bound cyclization mediated by BOP/HOBt/DIEA.

KW - allyl esters

KW - cyclic peptides

KW - orthogonal protection

KW - pseudo-dilution

KW - solid-phase synthesis

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides

Abstract

Keywords

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