A new amino acid derivative with a masked side-chain aldehyde and its use in peptide synthesis and chemoselective ligation

An unnatural amino acid derivative, N-tert-butyloxycarbonyl asparagine benzyl ester bearing a benzothiazole unit at the side chain, was evaluated as a fluorimetric chemosensor for several transition metal cations with environmental, biological and analytic relevance. Spectrofluorimetric titrations of the heterocyclic asparagine derivative with the various ions were carried out in acetonitrile and acetonitrile/water (9:1). It was found that the unnatural amino acid had a remarkable fluorimetric response in the presence of Cu2+ in acetonitrile and in the presence of Fe3+ in acetonitrile/water (9:1).

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Design of a fluorescent amino acid derivative usable in peptide synthesis

Tetrahedron Letters ◽

10.1016/s0040-4039(00)01007-8 ◽

2000 ◽

Vol 41 (32) ◽

pp. 6063-6066 ◽

Cited By ~ 18

Author(s):

Isabelle Dufau ◽

Honoré Mazarguil

Keyword(s):

Amino Acid ◽

Acid Derivative ◽

Peptide Synthesis ◽

Amino Acid Derivative ◽

Fluorescent Amino Acid

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A new non-natural arginine-like amino acid derivative with a sulfamoyl group in the side-chain

Amino Acids ◽

10.1007/s00726-009-0267-2 ◽

2009 ◽

Vol 38 (3) ◽

pp. 691-700 ◽

Cited By ~ 20

Author(s):

Rosaria De Marco ◽

Maria L. Di Gioia ◽

Antonella Leggio ◽

Angelo Liguori ◽

Francesca Perri ◽

...

Keyword(s):

Amino Acid ◽

Acid Derivative ◽

Amino Acid Derivative ◽

Side Chain

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Fmoc Solid Phase Peptide Synthesis

10.1093/oso/9780199637256.001.0001 ◽

1999 ◽

Cited By ~ 19

Keyword(s):

Peptide Synthesis ◽

Solid Phase ◽

Solid Phase Peptide Synthesis ◽

Peptide Chain ◽

Standard Approach ◽

Side Chain ◽

Complex Structures ◽

Protein Conjugation ◽

Chemoselective Ligation ◽

Routine Production

In the years since the publication of Atherton and Sheppard's volume, the technique of Fmoc solid-phase peptide synthesis has matured considerably and is now the standard approach for the routine production of peptides. The basic problems outstanding at the time of publication of this earlier work have now been, for the most part, solved. As a result, innovators in the field have focussed their efforts to develop methodologies and chemistry for the synthesis of more complex structures. The focus of this new volume is much broader, and covers not only the essential procedures for the production of linear peptides but also more advanced techniques for preparing cyclic, side-chain modified, phospho- and glycopeptides. Many other methods also deserving attention have been included: convergent peptide synthesis; peptide-protein conjugation; chemoselective ligation; and chemoselective purification. The difficult preparation of cysteine and methionine-containing peptides is also covered, as well as methods for overcoming aggregation during peptide chain assembly and a survey of available automated instrumentation.

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