Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity

Henryk Myszka , Patrycja Sokołowska , Agnieszka Cieślińska , Andrzej Nowacki , Maciej Jaśkiewicz , Wojciech Kamysz , Beata Liberek

Abstract

The synthesis of diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside is presented for the first time. This synthetic saponin was transformed into its hydrochloride as well as N-acyl, 2-ureido, N-alkyl, and N,N-dialkyl derivatives. Antifungal and antibacterial studies show that some of the obtained compounds are active against Gram-positive bacteria and Candida type fungi.
Author Henryk Myszka (FCh/DOCh/LG)
Henryk Myszka,,
- Laboratory of Glycochemistry
, Patrycja Sokołowska (FCh/DOCh/LG)
Patrycja Sokołowska,,
- Laboratory of Glycochemistry
, Agnieszka Cieślińska (FCh/DOCh/LG)
Agnieszka Cieślińska,,
- Laboratory of Glycochemistry
, Andrzej Nowacki (FCh/DOCh/LG)
Andrzej Nowacki,,
- Laboratory of Glycochemistry
, Maciej Jaśkiewicz - [Gdanski Uniwersytet Medyczny]
Maciej Jaśkiewicz,,
-
- Gdanski Uniwersytet Medyczny
, Wojciech Kamysz - [Gdanski Uniwersytet Medyczny]
Wojciech Kamysz,,
-
- Gdanski Uniwersytet Medyczny
, Beata Liberek (FCh/DOCh/LG)
Beata Liberek,,
- Laboratory of Glycochemistry
Other language title versions
Journal seriesBeilstein Journal of Organic Chemistry, ISSN 1860-5397, (A 30 pkt)
Issue year2017
Vol13
Pages2310-2315
Publication size in sheets0.30
Keywords in Englishantimicrobial activities, D-galactosamine, diosgenin, glycosylation, saponin, tetrachlorophthalimido derivative
ASJC Classification1605 Organic Chemistry
DOIDOI:10.3762/bjoc.13.227
URL http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-13-227.pdf?a=y
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa (CC-BY); with publication
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 31-07-2020, ArticleFromJournal
Publication indicators WoS Citations = 2.000; Scopus Citations = 3.000; Scopus SNIP (Source Normalised Impact per Paper): 2017 = 0.690; WoS Impact Factor: 2017 = 2.330 (2) - 2017=2.619 (5)
Citation count*6 (2020-08-01)
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