Sinteza derivatov L-arginina iz N-benziloksikarbonil-L-ornitina

Suhorepec, Nadja (author), Svete, Jurij (mentor)

V sklopu diplomskega dela smo želeli pripraviti del tetrapeptidne elektrofilne sonde, in sicer Arg(Boc)2-SerOMe (4). Uspešno smo sintetizirali N-Cbz-Arg(Boc)2-OH (1) iz N-Cbz-Orn(Boc)-OH in N,N'-Boc2-S-metilizotiosečnine. Spojino 1 smo nato spojili s serin metil estrom hidrokloridom v dipeptid N-Cbz-Arg(Boc)2-SerOMe (2) v prisotnosti treh različnih aktivacijskih reagentov: CDI, EEDQ in EDC. Pri tem se je kot stranski produkt tvoril α-N-benziloksikarbonil-ω,ω'-di-N-t-butoksikarbonil-L-arginin laktam (3). Poskus zmanjšanja deleža spojine 3 je bil neuspešen. V zadnjem koraku sinteze spojine 4 smo spojini 2 selektivno odstranili Cbz zaščitno skupino s katalitskim hidrogeniranjem.

• Language: Slovenian
• Keywords: dipeptid, aktivacijski reagenti, zaščitna skupina, hidrogenoliza
• Work type: Bachelor thesis/paper
• Typology: 2.11 - Undergraduate Thesis
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Year: 2022
• PID: 20.500.12556/RUL-139157
• COBISS.SI-ID: 122508291
• Publication date in RUL: 31.08.2022

Secondary language

• Language: English
• Title: Synthesis of derivatives of L-arginine from N-benzyloxycarbonyl-L-ornithine

Abstract

As a part of my Bachelor's thesis we aimed to prepare a part of a tetrapeptide electrophilic probe, namely Arg(Boc)2-SerOMe (4). N-Cbz-Arg(Boc)2-OH (1) was successfully synthesized from N-Cbz-Orn(Boc)-OH and N,N'-Boc2-Smethylisothiourea. Compound 1 was then coupled with serine methyl ester hydrochloride to the dipeptide N-Cbz-Arg(Boc)2-SerOMe (2) in the presence of three different coupling reagents: CDI, EEDQ and EDC. α-N-benzyloxycarbonyl-ω,ω'-di-N-tbutoxycarbonyl-L-arginine lactam (3) was formed as a by-product. An attempt to reduce the proportion of compoud 3 was unsuccessful. As a last step in the synthesis of compound 4, Cbz protecting group was selectively removed from compound 2 by catalytic hydrogenation.

• Keywords: dipeptide, coupling reagents, protecting group, hydrogenolysis