diplomsko delo
Nadja Suhorepec (Author), Jurij Svete (Mentor)

Abstract

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.

Keywords

dipeptidi;sinteza peptidov;aktivacijski reagenti;zaščitna skupina;hidrogenoliza;arginin;diplomska dela;

Data

Language: Slovenian
Year of publishing:
Typology: 2.11 - Undergraduate Thesis
Organization: UL FKKT - Faculty of Chemistry and Chemical Technology
Publisher: [N. Suhorepec]
UDC: 547.495.9.057(043.2)
COBISS: 122508291 Link will open in a new window
Views: 51
Downloads: 25
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Other data

Secondary language: English
Secondary title: Synthesis of derivatives of L-arginine from N-benzyloxycarbonyl-L-ornithine
Secondary 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.
Secondary keywords: dipeptide;coupling reagents;protecting group;hydrogenolysis;Peptidi;Univerzitetna in visokošolska dela;
Type (COBISS): Bachelor thesis/paper
Study programme: 1000373
Embargo end date (OpenAIRE): 1970-01-01
Thesis comment: Univ. v Ljubljani, Fak. za kemijo in kemijsko tehnologijo, UNI Kemija
Pages: 36 str.
ID: 16327073