Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

Jordi Alsina; George Barany; Fernando Albericio; Steven A. Kates

doi:10.1007/BF02443512

Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

Jordi Alsina, George Barany, Fernando Albericio, Steven A. Kates

Chemistry (Twin Cities)

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

4 Scopus citations

Abstract

Pyrrolidide derivatives are observed as unwanted by-products from slow reactions of activated carboxylates with nucleophilic amines, as mediated by phosphonium salt coupling reagents (PyAOP, PyBOP, PyBroP). This side reaction is attributed to the presence of small amounts (e.g., 0.5%, w/w) of pyrrolidine as a contaminant to commercial phosphonium salts, and does not occur when the reagents are crystallized before their use in coupling reactions.

Original language	English (US)
Pages (from-to)	243-245
Number of pages	3
Journal	International Journal of Peptide Research and Therapeutics
Volume	6
Issue number	4
DOIs	https://doi.org/10.1007/BF02443512
State	Published - 1999

Keywords

PyAOP
PyBOP
PyBroP
Side reactions
Solid-phase peptide synthesis

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10.1007/BF02443512

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title = "Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents",

abstract = "Pyrrolidide derivatives are observed as unwanted by-products from slow reactions of activated carboxylates with nucleophilic amines, as mediated by phosphonium salt coupling reagents (PyAOP, PyBOP, PyBroP). This side reaction is attributed to the presence of small amounts (e.g., 0.5%, w/w) of pyrrolidine as a contaminant to commercial phosphonium salts, and does not occur when the reagents are crystallized before their use in coupling reactions.",

keywords = "PyAOP, PyBOP, PyBroP, Side reactions, Solid-phase peptide synthesis",

author = "Jordi Alsina and George Barany and Fernando Albericio and Kates, {Steven A.}",

year = "1999",

doi = "10.1007/BF02443512",

language = "English (US)",

volume = "6",

pages = "243--245",

journal = "International Journal of Peptide Research and Therapeutics",

issn = "1573-3149",

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TY - JOUR

T1 - Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

AU - Alsina, Jordi

AU - Barany, George

AU - Albericio, Fernando

AU - Kates, Steven A.

PY - 1999

Y1 - 1999

N2 - Pyrrolidide derivatives are observed as unwanted by-products from slow reactions of activated carboxylates with nucleophilic amines, as mediated by phosphonium salt coupling reagents (PyAOP, PyBOP, PyBroP). This side reaction is attributed to the presence of small amounts (e.g., 0.5%, w/w) of pyrrolidine as a contaminant to commercial phosphonium salts, and does not occur when the reagents are crystallized before their use in coupling reactions.

AB - Pyrrolidide derivatives are observed as unwanted by-products from slow reactions of activated carboxylates with nucleophilic amines, as mediated by phosphonium salt coupling reagents (PyAOP, PyBOP, PyBroP). This side reaction is attributed to the presence of small amounts (e.g., 0.5%, w/w) of pyrrolidine as a contaminant to commercial phosphonium salts, and does not occur when the reagents are crystallized before their use in coupling reactions.

KW - PyAOP

KW - PyBOP

KW - PyBroP

KW - Side reactions

KW - Solid-phase peptide synthesis

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U2 - 10.1007/BF02443512

DO - 10.1007/BF02443512

M3 - Article

AN - SCOPUS:53149153583

SN - 1573-3149

VL - 6

SP - 243

EP - 245

JO - International Journal of Peptide Research and Therapeutics

JF - International Journal of Peptide Research and Therapeutics

IS - 4

ER -

Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

Abstract

Keywords

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