Hypersensitive acid-labile (HAL) tris(alkoxy)benzyl ester anchoring for solid-phase synthesis of protected peptide segments

Fernando Albericio; George Barany

doi:10.1016/S0040-4039(00)74475-3

Hypersensitive acid-labile (HAL) tris(alkoxy)benzyl ester anchoring for solid-phase synthesis of protected peptide segments

Fernando Albericio, George Barany

Chemistry (Twin Cities)

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

29 Scopus citations

Abstract

The novel 5-(4-hydroxymethyl-3,5-dimethoxyphenoxy)valeric acid (HAL) handle has been prepared and applied to solid-phase peptide synthesis using 9-fluorenylmethyloxycarbonyl (Fmoc) for N^α-amino protection and tert-butyl ethers, esters, and urethanes for side-chain protection. Otherwise fully protected peptide acids, which are needed for segment condensation studies, were obtained in excellent yields and purities by cleavage of the resultant tris(alkoxy)benzyl ester anchoring linkage with appropriate cocktails containing 0.5 - 0.1% (v/v) trifluoroacetic acid.

Original language	English (US)
Pages (from-to)	1015-1018
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(00)74475-3
State	Published - Feb 18 1991

Bibliographical note

Funding Information:
We thankD r. Derek Hudson of MilliGen/Biosearch for valuabled iscussionsa nd encouragementa,n d theN ational Institutes of Health (GM 28934 and 42722) and NATO (Collaborative Research Grant 0841/88)f or generous financial support.

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title = "Hypersensitive acid-labile (HAL) tris(alkoxy)benzyl ester anchoring for solid-phase synthesis of protected peptide segments",

abstract = "The novel 5-(4-hydroxymethyl-3,5-dimethoxyphenoxy)valeric acid (HAL) handle has been prepared and applied to solid-phase peptide synthesis using 9-fluorenylmethyloxycarbonyl (Fmoc) for Nα-amino protection and tert-butyl ethers, esters, and urethanes for side-chain protection. Otherwise fully protected peptide acids, which are needed for segment condensation studies, were obtained in excellent yields and purities by cleavage of the resultant tris(alkoxy)benzyl ester anchoring linkage with appropriate cocktails containing 0.5 - 0.1% (v/v) trifluoroacetic acid.",

author = "Fernando Albericio and George Barany",

note = "Funding Information: We thankD r. Derek Hudson of MilliGen/Biosearch for valuabled iscussionsa nd encouragementa,n d theN ational Institutes of Health (GM 28934 and 42722) and NATO (Collaborative Research Grant 0841/88)f or generous financial support.",

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doi = "10.1016/S0040-4039(00)74475-3",

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T1 - Hypersensitive acid-labile (HAL) tris(alkoxy)benzyl ester anchoring for solid-phase synthesis of protected peptide segments

AU - Albericio, Fernando

AU - Barany, George

N1 - Funding Information: We thankD r. Derek Hudson of MilliGen/Biosearch for valuabled iscussionsa nd encouragementa,n d theN ational Institutes of Health (GM 28934 and 42722) and NATO (Collaborative Research Grant 0841/88)f or generous financial support.

PY - 1991/2/18

Y1 - 1991/2/18

N2 - The novel 5-(4-hydroxymethyl-3,5-dimethoxyphenoxy)valeric acid (HAL) handle has been prepared and applied to solid-phase peptide synthesis using 9-fluorenylmethyloxycarbonyl (Fmoc) for Nα-amino protection and tert-butyl ethers, esters, and urethanes for side-chain protection. Otherwise fully protected peptide acids, which are needed for segment condensation studies, were obtained in excellent yields and purities by cleavage of the resultant tris(alkoxy)benzyl ester anchoring linkage with appropriate cocktails containing 0.5 - 0.1% (v/v) trifluoroacetic acid.

AB - The novel 5-(4-hydroxymethyl-3,5-dimethoxyphenoxy)valeric acid (HAL) handle has been prepared and applied to solid-phase peptide synthesis using 9-fluorenylmethyloxycarbonyl (Fmoc) for Nα-amino protection and tert-butyl ethers, esters, and urethanes for side-chain protection. Otherwise fully protected peptide acids, which are needed for segment condensation studies, were obtained in excellent yields and purities by cleavage of the resultant tris(alkoxy)benzyl ester anchoring linkage with appropriate cocktails containing 0.5 - 0.1% (v/v) trifluoroacetic acid.

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JO - Tetrahedron Letters

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SN - 0040-4039

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Hypersensitive acid-labile (HAL) tris(alkoxy)benzyl ester anchoring for solid-phase synthesis of protected peptide segments

Abstract

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