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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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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1724538632219394048 |