A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus

Jordi Alsina; T. Scott Yokum; Fernando Albericio; George Barany

doi:10.1016/S0040-4039(00)01255-7

A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus

Jordi Alsina, T. Scott Yokum, Fernando Albericio, George Barany

Chemistry (Twin Cities)

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

24 Scopus citations

Abstract

A new variation of the Backbone Amide Linker (BAL) approach has been developed for N(α)-Fmoc solid-phase synthesis (SPS) of C-terminal modified peptides; this provides a convenient route to peptides containing prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. To illustrate the principles, several model peptides were prepared in high yields and excellent purities; diketopiperazines and racemized byproducts which otherwise form when alternative procedures are used were absent from the syntheses reported herein. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	7277-7280
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	38
DOIs	https://doi.org/10.1016/S0040-4039(00)01255-7
State	Published - Sep 16 2000

Bibliographical note

Funding Information:
We are grateful to NATO (J.A.) and to NIH (T.S.Y., Grant GM 19460) for postdoctoral fellowships. This work was supported by CICYT (PB96-1490) and NIH (Grant GM 42722).

Keywords

Backbone amide linker
C-terminal modified peptides
Diketopiperazines
Histidine
Proline
PyBOP
Racemization

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title = "A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus",

abstract = "A new variation of the Backbone Amide Linker (BAL) approach has been developed for N(α)-Fmoc solid-phase synthesis (SPS) of C-terminal modified peptides; this provides a convenient route to peptides containing prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. To illustrate the principles, several model peptides were prepared in high yields and excellent purities; diketopiperazines and racemized byproducts which otherwise form when alternative procedures are used were absent from the syntheses reported herein. (C) 2000 Elsevier Science Ltd.",

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note = "Funding Information: We are grateful to NATO (J.A.) and to NIH (T.S.Y., Grant GM 19460) for postdoctoral fellowships. This work was supported by CICYT (PB96-1490) and NIH (Grant GM 42722).",

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AU - Alsina, Jordi

AU - Yokum, T. Scott

AU - Albericio, Fernando

AU - Barany, George

N1 - Funding Information: We are grateful to NATO (J.A.) and to NIH (T.S.Y., Grant GM 19460) for postdoctoral fellowships. This work was supported by CICYT (PB96-1490) and NIH (Grant GM 42722).

PY - 2000/9/16

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N2 - A new variation of the Backbone Amide Linker (BAL) approach has been developed for N(α)-Fmoc solid-phase synthesis (SPS) of C-terminal modified peptides; this provides a convenient route to peptides containing prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. To illustrate the principles, several model peptides were prepared in high yields and excellent purities; diketopiperazines and racemized byproducts which otherwise form when alternative procedures are used were absent from the syntheses reported herein. (C) 2000 Elsevier Science Ltd.

AB - A new variation of the Backbone Amide Linker (BAL) approach has been developed for N(α)-Fmoc solid-phase synthesis (SPS) of C-terminal modified peptides; this provides a convenient route to peptides containing prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus. To illustrate the principles, several model peptides were prepared in high yields and excellent purities; diketopiperazines and racemized byproducts which otherwise form when alternative procedures are used were absent from the syntheses reported herein. (C) 2000 Elsevier Science Ltd.

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KW - C-terminal modified peptides

KW - Diketopiperazines

KW - Histidine

KW - Proline

KW - PyBOP

KW - Racemization

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A modified Backbone Amide Linker (BAL) solid-phase peptide synthesis strategy accommodating prolyl, N-alkylamino acyl, or histidyl derivatives at the C-terminus

Abstract

Bibliographical note

Keywords

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