Application of the N-dibenzyl protective group in the preparation of β-lactam pseudopeptides

Frlan, Rok (author), Hrast, Martina (author), Gobec, Stanislav (author)

Despite the great importance of β-lactam antibiotics, there is still a limited number of synthetic approaches for the formation of β-lactam containing dipeptides. In this study, we report upon the stereoselective preparation of β-lactam-containing pseudopeptides, where different reaction conditions and NH$_2$ protective groups were tested to obtain compounds that contain 3-amino-azetidin-2-one. We demonstrate that the protective group is essential for the outcome of the reaction. Successful implementation of dibenzyl-protected serine-containing dipeptides through the Mitsunobu reaction can provide the desired products at high yields and stereoselectivity.

• Language: English
• Keywords: β-lactams, dibenzylamino, Mitsunobu reaction, nocardicin, pseudopeptides
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FFA - Faculty of Pharmacy
• Publication status: Published
• Publication version: Version of Record
• Year: 2019
• Number of pages: 15 str.
• Numbering: Vol. 24, iss. 7, art. 1261
• PID: 20.500.12556/RUL-132354
• UDC: 543.645.7:615.33
• ISSN on article: 1420-3049
• DOI: 10.3390/molecules24071261
• COBISS.SI-ID: 4699761
• Publication date in RUL: 22.10.2021

Record is a part of a journal

• Title: Molecules
• Shortened title: Molecules
• Publisher: MDPI
• ISSN: 1420-3049
• COBISS.SI-ID: 18462981

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 01.04.2019

Secondary language

• Language: Slovenian
• Keywords: antibiotiki

Projects

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