N-alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside: synthesis and antimicrobial activity

Agata Walczewska , Daria Grzywacz , Dorota Bednarczyk , Małgorzata Dawgul , Andrzej Nowacki , Wojciech Kamysz , Beata Liberek , Henryk Myszka


Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have no inhibitory activity against Gram-negative bacteria, whereas many of the tested N-alkyl saponins were found to inhibit the growth of Gram-positive bacteria and human pathogenic fungi.
Author Agata Walczewska (FCh / DOCh / LG)
Agata Walczewska ,,
- Laboratory of Glycochemistry
, Daria Grzywacz (FCh / DOCh / LG)
Daria Grzywacz,,
- Laboratory of Glycochemistry
, Dorota Bednarczyk - [Uniwersytet Gdanski]
Dorota Bednarczyk,,
- Uniwersytet Gdanski
, Małgorzata Dawgul - [Gdanski Uniwersytet Medyczny]
Małgorzata Dawgul,,
- Gdanski Uniwersytet Medyczny
, Andrzej Nowacki (FCh / DOCh / LG)
Andrzej Nowacki,,
- Laboratory of Glycochemistry
, Wojciech Kamysz - [Gdanski Uniwersytet Medyczny]
Wojciech Kamysz,,
- Gdanski Uniwersytet Medyczny
, Beata Liberek (FCh / DOCh / LG)
Beata Liberek,,
- Laboratory of Glycochemistry
, Henryk Myszka (FCh / DOCh / LG)
Henryk Myszka,,
- Laboratory of Glycochemistry
Journal seriesBeilstein Journal of Organic Chemistry, ISSN 1860-5397, (A 30 pkt)
Issue year2015
Publication size in sheets0.5
ASJC Classification1605 Organic Chemistry
URL http://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-11-97.pdf
Languageen angielski
LicenseJournal (articles only); published final; Uznanie Autorstwa (CC-BY); with publication
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 22-05-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 22-05-2020, ArticleFromJournal
Publication indicators WoS Citations = 7; Scopus Citations = 8; Scopus SNIP (Source Normalised Impact per Paper): 2015 = 0.791; WoS Impact Factor: 2015 = 2.697 (2) - 2015=2.844 (5)
Citation count*12 (2020-05-24)
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* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
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