ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS

ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS

Michael addition reactions involving nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives offer a concise and generalized methodological approach to synthesizing a family of χ-constrained five-carbon-atom amino acids. These amino acids play a crucial role in de novo pepti...

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Date:2024
Main Authors: Wzorek, Alicja, Sorochinsky, Alexander, Klika, Karel, Ono, Taizo, Han, Jianlin, Soloshonok, Vadim
Format: Article
Language:English
Published: V.I.Vernadsky Institute of General and Inorganic Chemistry 2024
Online Access:https://ucj.org.ua/index.php/journal/article/view/685
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Journal Title:Ukrainian Chemistry Journal

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Ukrainian Chemistry Journal
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spelling oai:ojs2.1444248.nisspano.web.hosting-test.net:article-6852025-03-03T14:00:35Z ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS Wzorek, Alicja Sorochinsky, Alexander Klika, Karel Ono, Taizo Han, Jianlin Soloshonok, Vadim Asymmetric synthesis, Michael additions, glycine equivalents, metal comp­lexes, Schiff bases, conformations, steric constrain. Glutamic acid, pyroglutamic acid, proline. Michael addition reactions involving nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives offer a concise and generalized methodological approach to synthesizing a family of χ-constrained five-carbon-atom amino acids. These amino acids play a crucial role in de novo peptide design and the elucidation of peptide/protein three-dimensional structures and their biological functions/activities. This review encapsulates the signi­ficant synthetic and methodological advancements in the field to date. Each method discussed includes an evaluation of synthetic opportunities and limitations, practicality and efficiency of the procedures, and mechanistic rationale behind the observed stereochemical preferences. V.I.Vernadsky Institute of General and Inorganic Chemistry 2024-09-27 Article Article Organic chemistry Органическая xимия Органічна xімія application/pdf https://ucj.org.ua/index.php/journal/article/view/685 10.33609/2708-129X.90.8.2024.83-108 Ukrainian Chemistry Journal; Vol. 90 No. 8 (2024): Ukrainian Chemistry Journal; 83-108 Украинский химический журнал; Том 90 № 8 (2024): Ukrainian Chemistry Journal; 83-108 Український хімічний журнал; Том 90 № 8 (2024): Ukrainian Chemistry Journal; 83-108 2708-129X 2708-1281 en https://ucj.org.ua/index.php/journal/article/view/685/340
institution Ukrainian Chemistry Journal
baseUrl_str
datestamp_date 2025-03-03T14:00:35Z
collection OJS
language English
topic_facet Asymmetric synthesis
Michael additions
glycine equivalents
metal comp­lexes
Schiff bases
conformations
steric constrain. Glutamic acid
pyroglutamic acid
proline.
format Article
author Wzorek, Alicja
Sorochinsky, Alexander
Klika, Karel
Ono, Taizo
Han, Jianlin
Soloshonok, Vadim
spellingShingle Wzorek, Alicja
Sorochinsky, Alexander
Klika, Karel
Ono, Taizo
Han, Jianlin
Soloshonok, Vadim
ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS
author_facet Wzorek, Alicja
Sorochinsky, Alexander
Klika, Karel
Ono, Taizo
Han, Jianlin
Soloshonok, Vadim
author_sort Wzorek, Alicja
title ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS
title_short ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS
title_full ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS
title_fullStr ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS
title_full_unstemmed ASYMMETRIC SYNTHESIS OF CHI-CONSTRAINED GLUTAMIC ACIDS AND RELATED COMPOUNDS VIA MICHAEL ADDITION REACTIONS
title_sort asymmetric synthesis of chi-constrained glutamic acids and related compounds via michael addition reactions
description Michael addition reactions involving nucleophilic glycine equivalents and α,β-unsaturated carboxylic acid derivatives offer a concise and generalized methodological approach to synthesizing a family of χ-constrained five-carbon-atom amino acids. These amino acids play a crucial role in de novo peptide design and the elucidation of peptide/protein three-dimensional structures and their biological functions/activities. This review encapsulates the signi­ficant synthetic and methodological advancements in the field to date. Each method discussed includes an evaluation of synthetic opportunities and limitations, practicality and efficiency of the procedures, and mechanistic rationale behind the observed stereochemical preferences.
publisher V.I.Vernadsky Institute of General and Inorganic Chemistry
publishDate 2024
url https://ucj.org.ua/index.php/journal/article/view/685
work_keys_str_mv AT wzorekalicja asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions
AT sorochinskyalexander asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions
AT klikakarel asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions
AT onotaizo asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions
AT hanjianlin asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions
AT soloshonokvadim asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions
first_indexed 2025-09-24T17:43:58Z
last_indexed 2025-09-24T17:43:58Z
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