AI Article Synopsis
- A new method has been developed for converting ribonucleosides into anti-HIV drugs like stavudine, zalcitabine, and didanosine using safer and cheaper reagents.
- This process leverages radical deoxygenation of xanthate and uses bromoethane or 3-bromopropanenitrile as alkylating agents, moving away from hazardous chemicals.
- Key substitutions include using tris(trimethylsilyl)silane and TBAF instead of more toxic reagents, alongside an enzyme to effectively produce ddI from 2',3'-dideoxyadenosine.
Article Abstract
An improved protocol for the transformation of ribonucleosides into 2',3'-dideoxynucleoside and 2',3'-didehydro-2',3'-dideoxynucleoside derivatives, including the anti-HIV drugs stavudine (d4T), zalcitabine (ddC) and didanosine (ddI), was established. The process involves radical deoxygenation of xanthate using environmentally friendly and low-cost reagents. Bromoethane or 3-bromopropanenitrile was the alkylating agent of choice to prepare the ribonucleoside 2',3'-bisxanthates. In the subsequent radical deoxygenation reaction, tris(trimethylsilyl)silane and 1,1'-azobis(cyclohexanecarbonitrile) were used to replace hazardous BuSnH and AIBN, respectively. In addition, TBAF was substituted for camphorsulfonic acid in the deprotection step of the 5'--silyl ether group, and an enzyme (adenosine deaminase) was used to transform 2',3'-dideoxyadenosine into 2',3'-dideoxyinosine (ddI) in excellent yield.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268517 | PMC |
| http://dx.doi.org/10.3390/molecules27133993 | DOI Listing |
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