Sodium borohydride: A versatile reagent in the reductive N-monoalkylation of α-amino acids and α-amino methyl esters

2002 ◽  
Vol 80 (7) ◽  
pp. 779-788 ◽  
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Elena Pol ◽  
Angelo G Giumanini
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Sodium Borohydride ◽  
Carbonyl Compounds ◽  
Condensation Reaction ◽  
Methyl Esters ◽  
Reducing Agent ◽  
Reductive Condensation ◽  
Versatile Reagent

α-Amino acids and α-amino methyl esters are easily converted to their N-monoalkyl derivatives by a reductive condensation reaction using several carbonyl compounds in the presence of sodium borohydride. This reducing agent has shown a wide versatility with minor but essential procedural variations. The reaction allows the α-monodeuterium labeling of the new N-substituent by use of sodium borodeuteride.Key words: α-amino acid, α-amino methyl esters, sodium borohydride, reductive N-monoalkylation, carbonyl compounds.

ChemInform Abstract: Sodium Borohydride: A Versatile Reagent in the Reductive N-Monoalkylation of α-Amino Acids and α-Amino Methyl Esters.

ChemInform ◽  
2010 ◽  
Vol 33 (48) ◽  
pp. no-no
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Elena Pol ◽  
Angelo G. Giumanini
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Methyl Esters ◽  
Versatile Reagent

Multifunctional lubricant additives derived from natural amino acids and methyl oleate

RSC Advances ◽  
2015 ◽  
Vol 5 (95) ◽  
pp. 77538-77544 ◽  
Author(s):  
Arukali Sammaiah ◽  
Korlipara V. Padmaja ◽  
Shiva Shanker Kaki ◽  
Rachapudi B. N. Prasad
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Oleate ◽  
Thioglycolic Acid ◽  
Methyl Esters ◽  
Lubricant Additives ◽  
Acid Methyl ◽  
Multifunctional Additives ◽  
Natural Amino Acids ◽  
Amino Acid Methyl Esters

Novel multifunctional additives were synthesized from methyl oleate via thioglycolic acid addition followed by condensation with different amino acid methyl esters.

Condensation Reaction Between α-Amino Acid Phenylhydrazides and Carbonyl Compounds.

ChemInform ◽  
2004 ◽  
Vol 35 (5) ◽  
Author(s):  
Giancarlo Verardo ◽  
Paola Geatti ◽  
Paolo Martinuzzi ◽  
Marcello Merli ◽  
Nicoletta Toniutti
Keyword(s):  
Amino Acid ◽  
Carbonyl Compounds ◽  
Condensation Reaction

GAS CHROMATOGRAPHIC METHOD FOR THE SEPARATION AND ESTIMATION OF AMINO ACID DERIVATIVES

1965 ◽  
Vol 43 (3) ◽  
pp. 309-315 ◽  
Author(s):  
P. B. Hagen ◽  
W. Black
Keyword(s):  
Amino Acids ◽  
Gas Chromatography ◽  
Amino Acid ◽  
Methyl Ester ◽  
Chromatographic Method ◽  
Methyl Esters ◽  
Amino Acid Derivatives ◽  
Constant Proportion ◽  
Gas Chromatographic Method

It has been possible to prepare the N-trifluoroacetyl methyl esters of the 19 amino acids commonly found in proteins and to separate them by gas chromatography on two types of column, Carbowax 1540 and Carbowax 20M. There is a constant relation between the amount of each amino acid and the size of the recorded peak. This indicates either that the conversion to the derivative is quantitative or that a constant proportion of each amino acid is converted to its N-trifluoroacetyl methyl ester.

Die Racemisierungs-Geschwindigkeit Schiffscher Basen von Aminosäure-estern / The Racemization of the Esters of N- (p-Nitrobenzylidene) -α-amino Acids

1971 ◽  
Vol 26 (8) ◽  
pp. 762-764 ◽  
Author(s):  
I. Z. Siemion ◽  
L. Wilschowitz
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Esters ◽  
Amino Acid Esters ◽  
Butyl Esters ◽  
Acid Esters

The racemization rate of N- [p-nitrobenzylidene] -α-amino acid esters was found to be even thousand-fold smaller than that of the azlactones of N-acyl-α-amino acids. t-Butyl esters of N-[p- nitrobenzylidene]-α-amino acids are much more stable to racemization as the correspondent methyl esters.

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