Abstract
(Chemical Equation Presented) In a study aimed at investigating an as yet unknown structure-activity relationship of the nikkomycin family of antifungal peptidyl nucleoside antibiotics, the present research reports the synthesis and antifungal evaluation of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B. Employing a convergent synthetic route, independent synthesis of the N-terminal amino acid side chain and a stereoselective de novo construction of the desired pyranosyl nucleoside amino acid fragment was followed by peptidic coupling of the two components, leading to the first synthesis of a carbohydrate ring-enlarged pyranosyl nikkomycin B analogue. In vitro biological evaluation of the above analogue against a variety of human pathogenic fungi demonstrated significant antifungal activity against several fungal strains of clinical significance.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 9991-9997 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 72 |
| Issue number | 26 |
| DOIs | |
| State | Published - Dec 21 2007 |
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ASJC Scopus subject areas
- Organic Chemistry
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Total synthesis and antifungal activity of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B. / Stauffer, Christina S.; Bhaket, Pushpal; Fothergill, Annette W.; Rinaldi, Michael G.; Datta, Apurba.
In: Journal of Organic Chemistry, Vol. 72, No. 26, 21.12.2007, p. 9991-9997.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis and antifungal activity of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B
AU - Stauffer, Christina S.
AU - Bhaket, Pushpal
AU - Fothergill, Annette W.
AU - Rinaldi, Michael G.
AU - Datta, Apurba
PY - 2007/12/21
Y1 - 2007/12/21
N2 - (Chemical Equation Presented) In a study aimed at investigating an as yet unknown structure-activity relationship of the nikkomycin family of antifungal peptidyl nucleoside antibiotics, the present research reports the synthesis and antifungal evaluation of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B. Employing a convergent synthetic route, independent synthesis of the N-terminal amino acid side chain and a stereoselective de novo construction of the desired pyranosyl nucleoside amino acid fragment was followed by peptidic coupling of the two components, leading to the first synthesis of a carbohydrate ring-enlarged pyranosyl nikkomycin B analogue. In vitro biological evaluation of the above analogue against a variety of human pathogenic fungi demonstrated significant antifungal activity against several fungal strains of clinical significance.
AB - (Chemical Equation Presented) In a study aimed at investigating an as yet unknown structure-activity relationship of the nikkomycin family of antifungal peptidyl nucleoside antibiotics, the present research reports the synthesis and antifungal evaluation of a carbohydrate ring-expanded pyranosyl nucleoside analogue of nikkomycin B. Employing a convergent synthetic route, independent synthesis of the N-terminal amino acid side chain and a stereoselective de novo construction of the desired pyranosyl nucleoside amino acid fragment was followed by peptidic coupling of the two components, leading to the first synthesis of a carbohydrate ring-enlarged pyranosyl nikkomycin B analogue. In vitro biological evaluation of the above analogue against a variety of human pathogenic fungi demonstrated significant antifungal activity against several fungal strains of clinical significance.
UR - http://www.scopus.com/inward/record.url?scp=37549045300&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37549045300&partnerID=8YFLogxK
U2 - 10.1021/jo701814b
DO - 10.1021/jo701814b
M3 - Article
C2 - 18001102
AN - SCOPUS:37549045300
VL - 72
SP - 9991
EP - 9997
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 26
ER -