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Diazotization of S-Sulfonyl-cysteines
[Image: see text] We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur’s nucleophilici...
| Autores principales: | , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical
Society
2019
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6862327/ https://www.ncbi.nlm.nih.gov/pubmed/31657562 http://dx.doi.org/10.1021/acs.joc.9b02630 |
| _version_ | 1783471529317629952 |
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| author | Mear, Sarah Jane Jamison, Timothy F. |
| author_facet | Mear, Sarah Jane Jamison, Timothy F. |
| author_sort | Mear, Sarah Jane |
| collection | PubMed |
| description | [Image: see text] We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur’s nucleophilicity by the anomeric effect. The key transformation was optimized by a 2(2) factorial design of experiment, highlighting the unique reactivity of cysteine derivatives in comparison with aliphatic amino acids. |
| format | Online Article Text |
| id | pubmed-6862327 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2019 |
| publisher | American Chemical
Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-68623272019-11-20 Diazotization of S-Sulfonyl-cysteines Mear, Sarah Jane Jamison, Timothy F. J Org Chem [Image: see text] We report the preparation of enantiomerically enriched β-thio-α-hydroxy and α-chloro carboxylic acid and ester building blocks by diazotization of S-sulfonyl-cysteines. The thiosulfonate protecting group demonstrated resistance to oxidation and attenuation of sulfur’s nucleophilicity by the anomeric effect. The key transformation was optimized by a 2(2) factorial design of experiment, highlighting the unique reactivity of cysteine derivatives in comparison with aliphatic amino acids. American Chemical Society 2019-10-28 2019-11-15 /pmc/articles/PMC6862327/ /pubmed/31657562 http://dx.doi.org/10.1021/acs.joc.9b02630 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
| spellingShingle | Mear, Sarah Jane Jamison, Timothy F. Diazotization of S-Sulfonyl-cysteines |
| title | Diazotization of S-Sulfonyl-cysteines |
| title_full | Diazotization of S-Sulfonyl-cysteines |
| title_fullStr | Diazotization of S-Sulfonyl-cysteines |
| title_full_unstemmed | Diazotization of S-Sulfonyl-cysteines |
| title_short | Diazotization of S-Sulfonyl-cysteines |
| title_sort | diazotization of s-sulfonyl-cysteines |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6862327/ https://www.ncbi.nlm.nih.gov/pubmed/31657562 http://dx.doi.org/10.1021/acs.joc.9b02630 |
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