Process improvement in amino acid N-carboxyanhydride synthesis by N-carbamoyl amino acid nitrosation

Autor: Olivier Lagrille, Laurent Boiteau, Jacques Taillades, Jean-Christophe Rossi, Grégoire Danger

Publikováno v: Amino Acids
Amino Acids, Springer Verlag, 2009, 36 (2), pp.341-347. ⟨10.1007/s00726-008-0090-1⟩

Amino acid N-carboxyanhydrides (NCA), convenient monomer for polypeptide synthesis, are easily prepared in high purity as the result of N-carbamoyl amino acids (CAA) nitrosation by gaseous NOx (4:1 NO + O2 mixture, or NOCl) in toluene. Removal of pol

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7ee3885524bee0d37fcef914dc736316
https://doi.org/10.1007/s00726-008-0090-1

From prebiotic macromolecules to synthetic polypeptides: a new, efficient synthesis of α-amino acidN-carboxyanhydrides (NCAs)

Autor: Laurent Boiteau, François Schué, Jacques Taillades, Auguste Commeyras, Olivia Giani, Olivier Lagrille, Hélène Collet, Willy Vayaboury

Publikováno v: Polymer International. 51:1037-1040

While polypeptide materials present important application potentialities, the expense of amino acid N-carboxyanhydride (NCA) monomers strongly limits their applications. We present here a new, promising synthetic route to NCA through N-carbamoylamino

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::e038e24079bcbbc781bb4cddbc271b11
https://doi.org/10.1002/pi.946

A pH-dependent cyanate reactivity model: application to preparative N-carbamoylation of amino acids

Autor: Willy Vayaboury, Isabelle Beuzelin, Odile Vandenabeele-Trambouze, Jacques Taillades, Auguste Commeyras, Olivier Lagrille, Jean-Philippe Biron, Laurent Boiteau, Olivia Giani

Publikováno v: Journal of the Chemical Society, Perkin Transactions 2. :1247-1254

Recent developments in peptide synthesis have underlined the importance of optimising, on a preparative scale, the N-carbamoylation of amino acids by aqueous cyanate. To this purpose, a theoretical model of aqueous cyanate reactivity was designed. Th

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::3ede00bcf1f3b454ac22cadae33f6a36
https://doi.org/10.1039/b005856o

Dynamic Co-evolution of Peptides and Chemical Energetics, a Gateway to the Emergence of Homochirality and the Catalytic Activity of Peptides

Autor: Raphaël Plasson, Odile Vandenabeele-Trambouze, Jacques Taillades, Laurent Boiteau, Hélène Collet, Hervé Martin, Jean-Christophe Rossi, Jean-Philippe Biron, Laurence Garrel, Robert Pascal, Eddy Souaid, Grégoire Danger, Franck Selsis, Michel Dobrijevic, Alain Rousset, Auguste Commeyras, Olivier Lagrille

Publikováno v: Origins of Life and Evolution of the Biosphere
Origins of Life and Evolution of the Biosphere, Springer-Verlag, 2004, 34 (1/2), pp.35-55. ⟨10.1023/B:ORIG.0000009827.54856.59⟩
ResearcherID

We propose a scenario for the dynamic co-evolution of peptides and energy on the primitive Earth. From a multi component system consisting of hydrogen cyanide, several carbonyl compounds, ammonia, alkyl amine, carbonic anhydride, borate and isocyanic

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ae53b6e5abbbb424fc153c812dcac702
https://hal.archives-ouvertes.fr/hal-03332600

N-carbamoyl derivatives and their nitrosation by gaseous NOx - A new, promising tool in stepwise peptide synthesis

Autor: Laurent Boiteau, Jacques Taillades, Olivier Lagrille, Auguste Commeyras

Publikováno v: ResearcherID

New uses of the N-carbamoyl group in peptide synthesis − as an Nα-protecting group in classical peptide coupling methods, and as a preactivating group for stepwise coupling by NCA formation − are presented. In the first application, the N-carbam

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::f4758fc8fc3898e413c3a410054ad222
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=ORCID&SrcApp=OrcidOrg&DestLinkType=FullRecord&DestApp=WOS_CPL&KeyUT=WOS:000174531400008&KeyUID=WOS:000174531400008