Synthesis of nonracemic hydroxyglutamic acids
Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses o...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2019-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.15.22 |
| _version_ | 1818556713699115008 |
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| author | Dorota G. Piotrowska Iwona E. Głowacka Andrzej E. Wróblewski Liwia Lubowiecka |
| author_facet | Dorota G. Piotrowska Iwona E. Głowacka Andrzej E. Wróblewski Liwia Lubowiecka |
| author_sort | Dorota G. Piotrowska |
| collection | DOAJ |
| description | Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses of nonracemic hydroxyglutamic acid analogues equipped with functional groups capable for the formation of additional hydrogen bonds, both as donors and acceptors. The majority of synthetic strategies starts from natural products and relies on application of chirons having the required configuration at the carbon atom bonded to nitrogen (e.g., serine, glutamic and pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered. |
| first_indexed | 2024-12-13T23:50:47Z |
| format | Article |
| id | doaj.art-435fe3d229be48a995a336981df800b5 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T23:50:47Z |
| publishDate | 2019-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-435fe3d229be48a995a336981df800b52022-12-21T23:26:47ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972019-01-0115123625510.3762/bjoc.15.221860-5397-15-22Synthesis of nonracemic hydroxyglutamic acidsDorota G. Piotrowska0Iwona E. Głowacka1Andrzej E. Wróblewski2Liwia Lubowiecka3Bioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandBioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandBioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandBioorganic Chemistry Laboratory, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, PolandGlutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses of nonracemic hydroxyglutamic acid analogues equipped with functional groups capable for the formation of additional hydrogen bonds, both as donors and acceptors. The majority of synthetic strategies starts from natural products and relies on application of chirons having the required configuration at the carbon atom bonded to nitrogen (e.g., serine, glutamic and pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered.https://doi.org/10.3762/bjoc.15.22amino acidsasymmetric synthesischiral catalysischiral poolglutamate analogues |
| spellingShingle | Dorota G. Piotrowska Iwona E. Głowacka Andrzej E. Wróblewski Liwia Lubowiecka Synthesis of nonracemic hydroxyglutamic acids Beilstein Journal of Organic Chemistry amino acids asymmetric synthesis chiral catalysis chiral pool glutamate analogues |
| title | Synthesis of nonracemic hydroxyglutamic acids |
| title_full | Synthesis of nonracemic hydroxyglutamic acids |
| title_fullStr | Synthesis of nonracemic hydroxyglutamic acids |
| title_full_unstemmed | Synthesis of nonracemic hydroxyglutamic acids |
| title_short | Synthesis of nonracemic hydroxyglutamic acids |
| title_sort | synthesis of nonracemic hydroxyglutamic acids |
| topic | amino acids asymmetric synthesis chiral catalysis chiral pool glutamate analogues |
| url | https://doi.org/10.3762/bjoc.15.22 |
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