A temporary marker for biological applications

M. Sameiro; T. Gonçalves; Hernâni L.S. Maia

doi:10.1016/S0040-4039(01)01350-8

A temporary marker for biological applications

M. Sameiro, T. Gonçalves, Hernâni L.S. Maia

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

8 Scopus citations

Abstract

Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.

Original language	English (US)
Pages (from-to)	7775-7777
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	44
DOIs	https://doi.org/10.1016/S0040-4039(01)01350-8
State	Published - Oct 29 2001

Bibliographical note

Funding Information:
We thank the Foundation for Science and Technology (Portugal) for financial support to the Institute of Biotechnology and Fine Chemistry (University of Minho).

Keywords

Acylation
Amino acid
Azo compounds
Cleavage reactions
Dyes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01350-8

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title = "A temporary marker for biological applications",

abstract = "Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.",

keywords = "Acylation, Amino acid, Azo compounds, Cleavage reactions, Dyes",

author = "M. Sameiro and T. Gon{\c c}alves and Maia, {Hern{\^a}ni L.S.}",

note = "Funding Information: We thank the Foundation for Science and Technology (Portugal) for financial support to the Institute of Biotechnology and Fine Chemistry (University of Minho).",

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doi = "10.1016/S0040-4039(01)01350-8",

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T1 - A temporary marker for biological applications

AU - Sameiro, M.

AU - Gonçalves, T.

AU - Maia, Hernâni L.S.

N1 - Funding Information: We thank the Foundation for Science and Technology (Portugal) for financial support to the Institute of Biotechnology and Fine Chemistry (University of Minho).

PY - 2001/10/29

Y1 - 2001/10/29

N2 - Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.

AB - Having in mind the development of new colour labelled amino acid derivatives, a carboxyl azo dye was coupled to amino acid esters to give the corresponding orange N-acyl derivatives, which were in turn further acylated at their N-terminus with Boc for investigation of the conditions of possible cleavage of the chromophore by electrolysis or with nucleophiles. While difficulties were met with electrolysis owing to competitive reduction of the azo group, cleavage with N,N-diethylaminoethylamine (DEAEA) gave satisfactory results. This allows the use of the chromophore as a temporary marker.

KW - Acylation

KW - Amino acid

KW - Azo compounds

KW - Cleavage reactions

KW - Dyes

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DO - 10.1016/S0040-4039(01)01350-8

M3 - Article

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EP - 7777

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 44

ER -

A temporary marker for biological applications

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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