N-Nosyl-α-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoe amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by 1H NMR and HPLC.

N-Nosyl-alpha-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/ sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoc amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by H-1 NMR and HPLC.

"One-Pot" methylation of N-nosyl-alpha-amino acid methyl esters with diazomethane and their coupling to prepare N-methyl dipeptides

DI GIOIA, Maria Luisa;LEGGIO, Antonella;Le Pera A;Liguori A;NAPOLI, Anna Maria Carmela Natale V;SICILIANO, Carlo;SINDONA, Giovanni
2003-01-01

Abstract

N-Nosyl-α-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoe amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by 1H NMR and HPLC.
2003
N-Nosyl-alpha-amino acid methyl esters are methylated quantitatively with diazomethane. After proper deprotection of the amino function by treatment with the reagent system mercaptoacetic acid/ sodium methoxide, the obtained N-methyl amino acid methyl esters are coupled with N-Fmoc amino acid chlorides to afford the corresponding dipeptides. The obtained products do not show any detectable extent of racemization by H-1 NMR and HPLC.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11770/126037
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