An efficient preparation of N-methyl-alpha-amino acids from N-nosyl-alpha-amino acid phenacyl esters. 2010

Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
Dipartimento di Scienze Farmaceutiche, Università della Calabria, Via Ponte P. Bucci Cubo 15/C, I-87036 Arcavacata di Rende (CS), Italy.

In this paper we describe a simple and efficient solution-phase synthesis of N-methyl-N-nosyl-alpha-amino acids and N-Fmoc-N-methyl-alpha-amino acids. This represents a very important application in peptide synthesis to obtain N-methylated peptides in both solution and solid phase. The developed methodology involves the use of N-nosyl-alpha-amino acids with the carboxyl function protected as a phenacyl ester and the methylating reagent diazomethane. An important aspect of this synthetic strategy is the possibility to selectively deprotect the carboxyl function or alternatively both amino and carboxyl moieties by using the same reagent with a different molar excess and under mild conditions. Furthermore, the adopted procedure keeps unchanged the acid-sensitive side chain protecting groups used in Fmoc-based synthetic strategies.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D010455 Peptides Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS. Peptide,Polypeptide,Polypeptides
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D000098 Acetophenones Derivatives of the simplest aromatic ketone acetophenone (of general formula C6H5C(O)CH3).
D000595 Amino Acid Sequence The order of amino acids as they occur in a polypeptide chain. This is referred to as the primary structure of proteins. It is of fundamental importance in determining PROTEIN CONFORMATION. Protein Structure, Primary,Amino Acid Sequences,Sequence, Amino Acid,Sequences, Amino Acid,Primary Protein Structure,Primary Protein Structures,Protein Structures, Primary,Structure, Primary Protein,Structures, Primary Protein
D000596 Amino Acids Organic compounds that generally contain an amino (-NH2) and a carboxyl (-COOH) group. Twenty alpha-amino acids are the subunits which are polymerized to form proteins. Amino Acid,Acid, Amino,Acids, Amino
D012996 Solutions The homogeneous mixtures formed by the mixing of a solid, liquid, or gaseous substance (solute) with a liquid (the solvent), from which the dissolved substances can be recovered by physical processes. (From Grant & Hackh's Chemical Dictionary, 5th ed) Solution
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

Related Publications

Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
January 2010, Amino acids,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
May 2007, The Journal of organic chemistry,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
September 2003, The Journal of organic chemistry,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
May 2010, The Journal of organic chemistry,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
December 2004, Chemical reviews,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
May 1977, The Journal of organic chemistry,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
January 1939, The Biochemical journal,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
June 1997, The journal of peptide research : official journal of the American Peptide Society,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
January 1971, Chemische Berichte,
Antonella Leggio, and Emilia Lucia Belsito, and Rosaria De Marco, and Angelo Liguori, and Francesca Perri, and Maria Caterina Viscomi
August 2005, The Journal of organic chemistry,
Copied contents to your clipboard!