A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]pentanedioic acid, monoamide (PBS) handle

Daniel G. Mullen; George Barany

doi:10.1016/S0040-4039(00)95763-0

A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]pentanedioic acid, monoamide (PBS) handle

Daniel G. Mullen, George Barany

Chemistry (Twin Cities)

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24 Scopus citations

Abstract

The synthesis and characterization of a new silicon-containing handle for use in solid-phase peptide synthesis is described. The anchoring linkage derived from this new handle, when treated with fluoride (1.0 equiv.) for 5 min at 25 °C, releases peptides as their free acids in essentially quantitative yields and without racemization.

Original language	English (US)
Pages (from-to)	491-494
Number of pages	4
Journal	Tetrahedron Letters
Volume	28
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(00)95763-0
State	Published - 1987

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A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]pentanedioic acid, monoamide (PBS) handle. / Mullen, Daniel G.; Barany, George.
In: Tetrahedron Letters, Vol. 28, No. 5, 1987, p. 491-494.

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

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title = "A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]pentanedioic acid, monoamide (PBS) handle",

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T2 - Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]pentanedioic acid, monoamide (PBS) handle

AU - Mullen, Daniel G.

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AB - The synthesis and characterization of a new silicon-containing handle for use in solid-phase peptide synthesis is described. The anchoring linkage derived from this new handle, when treated with fluoride (1.0 equiv.) for 5 min at 25 °C, releases peptides as their free acids in essentially quantitative yields and without racemization.

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A new fluoridolysable anchoring linkage for orthogonal solid-phase peptide synthesis: Preparation and properties of the N-(3 or 4)-[[[(4-hydroxymethyl)-phenoxy-t-butylphenyl]silyl]phenyl]pentanedioic acid, monoamide (PBS) handle

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