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The synthesis of (2R)-aziridine-2-carboxylic acid containing dipeptides
ID Kuzmič, Samo (Author), ID Hrast, Martina (Author), ID Frlan, Rok (Author)

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Abstract
Optimized conditions for the synthesis of fully deprotected (2R)-aziridine containing dipeptides are described. Preparation of fully protected N- and C- terminal aziridine containing dipeptides was found to be straightforward and high yielding for the majority of compounds, whereas their full deprotection was possible only for C-terminal analogs. Deprotection of N-terminal derivatives using standard procedures of peptide chemistry was found difficult providing only mixtures of unidentifiable products. The described molecules have potential as building blocks in synthetic chemistry, in the chemical biology arena, as covalent modifiers, and as biomarkers.

Language:English
Keywords:dipeptides, aziridines, biomarkers, warheads, antibacterial agents
Work type:Article
Typology:1.01 - Original Scientific Article
Organization:FFA - Faculty of Pharmacy
Publication status:Published
Publication version:Version of Record
Year:2022
Number of pages:Str. 261-270
Numbering:no. 2, Vol. 69
PID:20.500.12556/RUL-142817 This link opens in a new window
UDC:543.645.6.057
ISSN on article:1580-3155
DOI:10.17344/acsi.2021.6673 This link opens in a new window
COBISS.SI-ID:108102659 This link opens in a new window
Publication date in RUL:28.11.2022
Views:916
Downloads:407
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Record is a part of a journal

Title:Acta chimica slovenica
Shortened title:Acta chim. slov.
Publisher:Slovensko kemijsko društvo, =Slovenian Chemical Society
ISSN:1580-3155
COBISS.SI-ID:21870085 This link opens in a new window

Secondary language

Language:Slovenian
Abstract:
V prispevku so opisani optimizirani pogoji za sintezo dipeptidov, ki vsebujejo popolnoma odščiten (2R)-aziridin. Priprava popolnoma zaščitenih N- in C- terminalnih dipeptidov, ki vsebujejo aziridin, je enostavna in poteka z visokim izkoristkom za večino spojin, medtem ko je njihova popolna odščita možna le za C-terminalne analoge. Odstranjevanje zaščite z N-terminalnih derivatov z uporabo standardnih postopkov peptidne kemije se je izkazalo kot težko, saj vodi do mešanice nedoločljivih produktov. Opisane molekule imajo velik potencial kot gradniki v sintezni kemiji, na področju kemijske biologije, kot kovalentni modifikatorji in kot biomarkerji.

Keywords:dipeptidi, aziridini, biomarkerji, bojne glave, antibakterijska sredstva

Projects

Funder:ARRS - Slovenian Research Agency
Project number:P1-0208-2015
Name:Farmacevtska kemija: načrtovanje, sinteza in vrednotenje učinkovin

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