Synthesis of (E)-2- Chlorhomovinyl Ribose to Examine the Mechanism of 6-Chlorhomovinyl Adenosine

Nucleosides function as important agents in fundamental human metabolism and provide a broad range of activity in resulting modification of these nucleosides as functional prodrugs. Various modified nucleosides exhibit inhibitory activity towards enzymes and carry the possibility of containing anti-viral and anti-cancer properties. These properties are often exhibited by modifying the nucleobase moiety or the sugar moiety as synthesized novel nucleosides. In understanding my project aim, the sugar moiety of 6-chlorohomovinyl adenosine will be synthesized as the novel nucleoside (E)-2-chlorovinylribose to examine the nucleoside as the active component of 6-chlorohomovinyl adenosine. 6-chlorohomovinyl adenosine 1 demonstrates an active component that works specifically against Trypanosoma Brucei, a parasite associated with African trypanosomiasis, which is a widespread disease within East and South Africa. This compound has also demonstrated positive results within animal testing and is in the second phase of drug testing. As the sugar analog of 1, (E)-2-chlorovinylribose 4 will be examined to understand the mechanistic properties and active sites of 1. The proposed synthesis for the target compound begins with oxidative cleavage at C5 and C6 of 2 which is commercially available and is the primary source needed to make the desired product in addition to the necessary reactive agents. Followed by benzyl substitution, 2 is converted into 3 by the means of periodic acid and ethyl acetate and formed into the 5’OH-ribose by the means of sodium borohydride reduction. Furthermore, Moffatt oxidation followed by Wittig homologation with the tosylated ylide (PPh3CH=Ts), Bu3SnH with AIBN is expressed on the compound to propagate a new bond on the 6’ Carbon for conversion into the desired chloro group on 6’C. Then, deprotection of the isopropyl group and the benzyl group are formed to the target 4. This synthesis of compound 4 would provide as the evidence as to how 1 function within the cell environmen

Bob Dylan and that "Italian Poet from the Thirteenth Century"

Beginning with a verse in Bob Dylan's "Tangled up in Blue" that details two characters reading a book of poems by an unnamed Italian poet from the thirteenth century, the direct and 'diffused' influence of Dante upon the great American songwriter and Nobel Laurate is investigated. Further, a possibly intentional narrative similarity is proposed between the story told in "Tangled up in Blue" and the one Francesca tells in Inferno 5. After exploring the available evidence regarding the explicit influence of Dante's work upon the songwriter, and other hypotheses related to the verse from this song in particular, sources for Dante's diffused influence upon Dylan are discussed. With often enigmatic lyrics and elusive statements, this latter point regarding Dante's abundant presence in literary works we know Dylan read confirms the role Dante plays-in one way or another-within Dylan's lyrical oeuvre, even if the identity of that thirteenth century Italian poet in the song will likely remain a mystery.A partire da un verso di "Tangled up in Blue" di Bob Dylan che descrive due personaggi che leggono un libro di poesie di un poeta italiano del XIII secolo, si indaga l'influenza diretta e 'diffusa' di Dante sul grande cantautore americano e Premio Nobel. Inoltre, viene proposta una somiglianza narrativa forse intenzionale tra la storia raccontata in "Tangled up in Blue" e quella che Francesca racconta in Inferno 5. Dopo aver esaminato le prove disponibili riguardanti l'influenza esplicita dell'opera di Dante sul cantautore, e altre ipotesi relative al verso di questa canzone in particolare, viene affrontata la questione delle fonti dell'influenza diffusa di Dante su Dylan. Sviluppato per mezzo di testi spesso enigmatici e affermazioni elusive, quest'ultimo aspetto, quello cioè riguardante l'abbondante presenza di Dante nelle opere letterarie che sappiamo lette da Dylan, conferma il ruolo di Dante, in un modo o nell'altro, nell'opera lirica el cantautore, anche se l'identità del poeta italiano del XIII secolo nella canzone rimarrà probabilmente un mistero