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Publication
- 2015 Aug 10

α-Amino acid N-Carboxy Anhydrides in pharmaceutical innovations: try them to capture new value

Yves Robin, Chemistry Today , 33(4) July-August 2015 - Yves Robin

http://www.teknoscienze.com/articles/chimica-oggi-chemistry-today--alph…

An overview of NCA innovations are shown below in three main points:

  1. The preparation of NCA building blocks from an industrial perspective.
  2. The key role of NCAs in pharmaceutical applications and
  3. The value of NCAs compared with other synthetic strategies of α-Amino acid couplings will be described.

Keywords

α-amino acid N-Carboxy Anhydrides, NCA, Urethane α-Amino acid N-Carboxy Anhydrides, UNCA, Ring Opening Polymerization, ROP, Peptide, Polypeptide, Polyamino acid, Amino acid coupling, Drug delivery, Active pharmaceutical ingredient.

Abstract

α-Amino acid α-Carboxy Anhydrides (NCA) have been discovered over a century ago (1). The first significant development and use of NCAs in the pharmaceutical industry started during the second half of the 20th century while the interest of chemists revealed three major areas for innovation: 1) their preparation 2) their use in ring opening polymerization and copolymerization (ROP) reactions for polyamino acid synthesis and 3) their use in coupling reactions for α-amino acid derivatives or peptide fragment synthesis.

Publication
- 2015 Jan 03

Using Tocophersolan for Drug Delivery

A natural Vitamin E derivative is an innovative excipient - Yves Robin, Pharmaceutical Technology - January 2015

https://www.pixelmags.com/awrv1/#magazines/1367/issues/110846/pages/51

Abstract

Tocophersolan or d-α-tocopheryl polyethylene glycol succinate (TPGS) was developed 60 years ago as a water-soluble form of vitamin E. Its surfactant properties triggered the interest of drug formulation developers before it steadily moved into the toolbox of pharmaceutical drug-delivery innovators. The author gives an overview of TPGS, including its interesting properties, examples found in the literature, and a brief summary of the regulatory status and marketed formulations.

Publication
- 2015 Jan 02

Controlled Ring Opening of N-Sulfinyl- and N-Silyl-N-carboxyanhydrides (NCA)

One-Pot Synthesis of Dipeptides and Unsymmetrical Peptidyl Ureas from Unprotected NCA, Synthesis of Dipeptides and Unsymmetrical Peptidyl Ureas

Julia Mateos-Caro, Yves Robin, Vincent Levacher,* Francis Marsais , Synlett 2009 pp 279-283

Keywords

N-protected carboxyanhydrides (NCA) - peptidyl ­ureas - dipeptides

Abstract

We report herein new labile protecting groups of N-carboxyanhydrides (NCA) useful to prevent polymerization during coupling reactions with nitrogen nucleophiles. Thus, N-sulfinyl-NCA 1 and N-silyl-NCA 2 were prepared in situ and involved, without being isolated, in coupling reactions with various α-amino esters to furnish dipeptides 3 and unsymmetrical peptidyl ureas 4, respectively, in good yields.