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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| Datum: | 2024 |
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| Sprache: | English |
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V.I.Vernadsky Institute of General and Inorganic Chemistry
2024
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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 |
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AT wzorekalicja asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions AT sorochinskyalexander asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions AT klikakarel asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions AT onotaizo asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions AT hanjianlin asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions AT soloshonokvadim asymmetricsynthesisofchiconstrainedglutamicacidsandrelatedcompoundsviamichaeladditionreactions |
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2025-09-24T17:43:58Z |
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2025-09-24T17:43:58Z |
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