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Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins

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Summary

Some of the chemistry of amino acids going on in our laboratory (Laboratoire des Amino acides Peptides et Protéines) is described as well as some mass spectrometry methodology for their characterization particularly on solid supports. Several aspects are presented including: (i) the stereoselective synthesis of natural and unnatural amino acids using 2-hydroxypinan-3-one as chiral auxiliary; (ii) the stereoselective synthesis of natural and unnatural amino acids by deracemization ofα-amino acidsvia their ketene derivatives; (iii) the synthesis ofα-aryl-α-amino acidsvia reaction of organometallics with a glycine cation; (iv) the diastereoselective synthesis of glycosyl-α-amino acids; (v) the synthesis ofβ-amino acids using a-aminopyrrolidinopiperazinediones as chiral templates; (vi) the reactivity of urethane-N-protected N-carboxyanhydrides. To characterize natural and non natural amino acids through their immonium ions by mass spectrometry, some methodology is also described.

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Abbreviations

Boc:

tert-butyloxycarbonyl

BOP:

benzotriazol-1-yl-oxytris(dimethylamino) phosphonium hexafluorophosphate

CAD:

Collision Activated Dissociation

DCC:

N,N′-dicyclohexylcarbodiimide

DIEA:

diisopropylethylamine

DMAP:

dimethylaminopyridine

FAB:

Fast Atom Bombardment

HOBt:

1-hydroxybenzotriazole

H.P.:

2-hydroxypinan-3-one

NMM:

N-methylmorpholine

PEG:

polyethylene glycol

SIMS:

Secondary Ion Mass Spectrometry

TEA:

triethylamine

UNCAs:

urethane N-protected N-carboxyanhydrides

Z-:

Benzyloxycarbonyle

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  1. UNIR 5810, Universités Montpellier II et I, Place E. Bataillon, F-34095, Montpellier Cédex 05, France

    S. Bouifraden, C. Drouot, M. El Hadrami, F. Guenoun, L. Lecointe, N. Mai, M. Paris, C. Pothion, M. Sadoune, B. Sauvagnat, M. Amblard, J. L. Aubagnac, M. Calmes, P. Chevallet, J. Daunis, C. Enjalbal, J. A. Fehrentz, F. Lamaty, J. P. Lavergne, R. Lazaro, V. Rolland, M. L. Roumestant, Ph. Viallefont, Y. Vidal &  J. Martinez

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  1. S. Bouifraden
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  2. C. Drouot
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  22. M. L. Roumestant
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Bouifraden, S., Drouot, C., El Hadrami, M. et al. Some of the amino acid chemistry going on in the Laboratory of Amino Acids, Peptides and Proteins. Amino Acids 16, 345–379 (1999). https://doi.org/10.1007/BF01388176

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