Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline
We present a recipe for the stereoselective conversion of commercial (<i>cis</i>)-4-hydroxy-L-proline into (<i>4S</i>)-1-methyl-4-propyl-L-proline, an analog of the amino acid fragment found in the clinically used antibacterial antibiotic lincomycin. The single-crystal X-ray...
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MDPI AG
2025-05-01
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| author | Gour Hari Mandal Shifali Choudhary Steven P. Kelley Shyam Sathyamoorthi |
| author_facet | Gour Hari Mandal Shifali Choudhary Steven P. Kelley Shyam Sathyamoorthi |
| author_sort | Gour Hari Mandal |
| collection | DOAJ |
| description | We present a recipe for the stereoselective conversion of commercial (<i>cis</i>)-4-hydroxy-L-proline into (<i>4S</i>)-1-methyl-4-propyl-L-proline, an analog of the amino acid fragment found in the clinically used antibacterial antibiotic lincomycin. The single-crystal X-ray diffraction analysis of the final target’s hydrochloride salt confirms its identity and absolute stereochemistry. |
| format | Article |
| id | doaj-art-a1b7dfbc4eb147f6aef94c1ee424532f |
| institution | Matheson Library |
| issn | 1422-8599 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj-art-a1b7dfbc4eb147f6aef94c1ee424532f2025-06-25T14:13:15ZengMDPI AGMolbank1422-85992025-05-0120252M200310.3390/M2003Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-prolineGour Hari Mandal0Shifali Choudhary1Steven P. Kelley2Shyam Sathyamoorthi3Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66047, USADepartment of Medicinal Chemistry, University of Kansas, Lawrence, KS 66047, USADepartment of Chemistry, University of Missouri—Columbia, Columbia, MO 65211, USADepartment of Medicinal Chemistry, University of Kansas, Lawrence, KS 66047, USAWe present a recipe for the stereoselective conversion of commercial (<i>cis</i>)-4-hydroxy-L-proline into (<i>4S</i>)-1-methyl-4-propyl-L-proline, an analog of the amino acid fragment found in the clinically used antibacterial antibiotic lincomycin. The single-crystal X-ray diffraction analysis of the final target’s hydrochloride salt confirms its identity and absolute stereochemistry.https://www.mdpi.com/1422-8599/2025/2/M2003amino acidsantibiotic analogsstereoselective synthesis |
| spellingShingle | Gour Hari Mandal Shifali Choudhary Steven P. Kelley Shyam Sathyamoorthi Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline Molbank amino acids antibiotic analogs stereoselective synthesis |
| title | Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline |
| title_full | Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline |
| title_fullStr | Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline |
| title_full_unstemmed | Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline |
| title_short | Stereoselective Preparation of (<i>4S</i>)-1-Methyl-4-propyl-L-proline Commencing from (<i>cis</i>)-4-Hydroxy-L-proline |
| title_sort | stereoselective preparation of i 4s i 1 methyl 4 propyl l proline commencing from i cis i 4 hydroxy l proline |
| topic | amino acids antibiotic analogs stereoselective synthesis |
| url | https://www.mdpi.com/1422-8599/2025/2/M2003 |
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