4-alkoxy-2-hydroxybenzaldehyde (AHB): A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics

Toru Okayama; Andrew Burritt; Victor J. Hruby

doi:10.1021/ol000048h

4-alkoxy-2-hydroxybenzaldehyde (AHB): A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics

Toru Okayama, Andrew Burritt, Victor J. Hruby

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

19 Scopus citations

Abstract

(Formula presented) A new and versatile 4-alkoxy-2-hydroxybenzaldehyde (AHB) linker for solid-phase syntheses is described. Acylation of the polymer-bound secondary amine obtained from reductive amination of the aldehyde in the AHB linker showed good reactivity. Following acylation of the phenolic hydroxyl group, the resulting carboxamide resin was stable to treatment with 95% TFA. The O-acyl functional group was removed with 20% piperidine and the desired compound was cleaved from the resin by TFA treatment.

Original language	English (US)
Pages (from-to)	1787-1790
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	13
DOIs	https://doi.org/10.1021/ol000048h
State	Published - Jun 29 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol000048h

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title = "4-alkoxy-2-hydroxybenzaldehyde (AHB): A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics",

abstract = "(Formula presented) A new and versatile 4-alkoxy-2-hydroxybenzaldehyde (AHB) linker for solid-phase syntheses is described. Acylation of the polymer-bound secondary amine obtained from reductive amination of the aldehyde in the AHB linker showed good reactivity. Following acylation of the phenolic hydroxyl group, the resulting carboxamide resin was stable to treatment with 95% TFA. The O-acyl functional group was removed with 20% piperidine and the desired compound was cleaved from the resin by TFA treatment.",

author = "Toru Okayama and Andrew Burritt and Hruby, {Victor J.}",

year = "2000",

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T2 - A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics

AU - Okayama, Toru

AU - Burritt, Andrew

AU - Hruby, Victor J.

PY - 2000/6/29

Y1 - 2000/6/29

N2 - (Formula presented) A new and versatile 4-alkoxy-2-hydroxybenzaldehyde (AHB) linker for solid-phase syntheses is described. Acylation of the polymer-bound secondary amine obtained from reductive amination of the aldehyde in the AHB linker showed good reactivity. Following acylation of the phenolic hydroxyl group, the resulting carboxamide resin was stable to treatment with 95% TFA. The O-acyl functional group was removed with 20% piperidine and the desired compound was cleaved from the resin by TFA treatment.

AB - (Formula presented) A new and versatile 4-alkoxy-2-hydroxybenzaldehyde (AHB) linker for solid-phase syntheses is described. Acylation of the polymer-bound secondary amine obtained from reductive amination of the aldehyde in the AHB linker showed good reactivity. Following acylation of the phenolic hydroxyl group, the resulting carboxamide resin was stable to treatment with 95% TFA. The O-acyl functional group was removed with 20% piperidine and the desired compound was cleaved from the resin by TFA treatment.

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4-alkoxy-2-hydroxybenzaldehyde (AHB): A versatile aldehyde linker for solid-phase synthesis of C-terminal modified peptides and peptidomimetics

Abstract

ASJC Scopus subject areas

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