Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure

Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure

γ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, <i>N</i>-phtaloyl-<span style="font-var...

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Main Authors: Giovanna Speranza, Marco Rabuffetti, Nikolina Vidović, Carlo F. Morelli
Format: Article
Language:English
Published: MDPI AG 2020-07-01
Series:Molbank
Subjects:
γ-glutamyl compounds
sulfur amino acids
one-pot synthesis
taste-active compounds
kokumi
Online Access:https://www.mdpi.com/1422-8599/2020/3/M1147
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spelling doaj-a45efb6661b1409fac00114ea8a7cf382020-11-25T03:39:28ZengMDPI AGMolbank1422-85992020-07-012020M1147M114710.3390/M1147Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot ProcedureGiovanna Speranza0Marco Rabuffetti1Nikolina Vidović2Carlo F. Morelli3Dipartimento di Chimica, Università degli Studi di Milano via Golgi, 19-20133 Milano, ItalyDipartimento di Scienze per gli Alimenti, la Nutrizione e l’Ambiente, Università degli Studi di Milano via Celoria, 2-20133 Milano, ItalyDipartimento di Chimica, Università degli Studi di Milano via Golgi, 19-20133 Milano, ItalyDipartimento di Chimica, Università degli Studi di Milano via Golgi, 19-20133 Milano, Italyγ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, <i>N</i>-phtaloyl-<span style="font-variant: small-caps;">l</span>-glutamic acid anhydride is obtained from <span style="font-variant: small-caps;">l</span>-glutamic acid and phtalic anhydride. In the second one, <i>N</i>-phtaloyl-<span style="font-variant: small-caps;">l</span>-glutamic acid anhydride is used to acylate amino acids and the <i>N</i>-phtaloyl protecting group is removed. The described approach offers a viable entry to γ-glutamyl derivatives of sulfur-containing amino acids with flavor-enhancer and nutraceutical properties.https://www.mdpi.com/1422-8599/2020/3/M1147γ-glutamyl compoundssulfur amino acidsone-pot synthesistaste-active compoundskokumi
collection DOAJ
language English
format Article
sources DOAJ
author Giovanna Speranza
Marco Rabuffetti
Nikolina Vidović
Carlo F. Morelli
spellingShingle Giovanna Speranza
Marco Rabuffetti
Nikolina Vidović
Carlo F. Morelli
Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure
Molbank
γ-glutamyl compounds
sulfur amino acids
one-pot synthesis
taste-active compounds
kokumi
author_facet Giovanna Speranza
Marco Rabuffetti
Nikolina Vidović
Carlo F. Morelli
author_sort Giovanna Speranza
title Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure
title_short Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure
title_full Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure
title_fullStr Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure
title_full_unstemmed Synthesis of γ-Glutamyl Derivatives of Sulfur-Containing Amino Acids in a Multigram Scale via a Two-Step, One-Pot Procedure
title_sort synthesis of γ-glutamyl derivatives of sulfur-containing amino acids in a multigram scale via a two-step, one-pot procedure
publisher MDPI AG
series Molbank
issn 1422-8599
publishDate 2020-07-01
description γ-Glutamyl derivatives of sulfur amino acids have been prepared in multigram scale starting from readily available starting materials. The synthesis comprises two one-pot operations, both consisting of two reactions. In the first operation, <i>N</i>-phtaloyl-<span style="font-variant: small-caps;">l</span>-glutamic acid anhydride is obtained from <span style="font-variant: small-caps;">l</span>-glutamic acid and phtalic anhydride. In the second one, <i>N</i>-phtaloyl-<span style="font-variant: small-caps;">l</span>-glutamic acid anhydride is used to acylate amino acids and the <i>N</i>-phtaloyl protecting group is removed. The described approach offers a viable entry to γ-glutamyl derivatives of sulfur-containing amino acids with flavor-enhancer and nutraceutical properties.
topic γ-glutamyl compounds
sulfur amino acids
one-pot synthesis
taste-active compounds
kokumi
url https://www.mdpi.com/1422-8599/2020/3/M1147
work_keys_str_mv AT giovannasperanza synthesisofgglutamylderivativesofsulfurcontainingaminoacidsinamultigramscaleviaatwosteponepotprocedure
AT marcorabuffetti synthesisofgglutamylderivativesofsulfurcontainingaminoacidsinamultigramscaleviaatwosteponepotprocedure
AT nikolinavidovic synthesisofgglutamylderivativesofsulfurcontainingaminoacidsinamultigramscaleviaatwosteponepotprocedure
AT carlofmorelli synthesisofgglutamylderivativesofsulfurcontainingaminoacidsinamultigramscaleviaatwosteponepotprocedure
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