Structural elucidation of aculeximycin. II. Structures of carbohydrate moieties.
Treatment of aculeximycin with 2% 1,8-diazabicyclo[5,4,0]undecene-7 (DBU)-methanol yielded three products, aculexitriose, pseudoaglycones I and II. The structural elucidation of aculexitriose was carried out by spectral analyses (MS, NMR (1H-1H 2D NMR spectroscopy, nuclear Overhauser effect] and chemical degradations of aculexitriose and its derivatives. The structure of aculexitriose was established to be a branched trisaccharide, O-6-deoxy-beta-D-glucopyranosyl-(1----2)-O-[3-amino-2,3,6-trideoxy-beta- D- arabino-hexopyranosyl-(1----3)]-6-deoxy-D-glucopyranose. On the other hand the pseudoaglycones I and II were stereoisomers with respect to a chiral center newly formed by the DBU reaction. The pseudoaglycones contain one neutral sugar and one amino sugar, which turned out to be D-mannose and L-vancosamine, respectively.
Murata
H
H
Faculty of Pharmacy, Meijo University, Nagoya, Japan.
Harada
K
K
Suzuki
M
M
Ikemoto
T
T
Shibuya
T
T
Haneishi
T
T
Torikata
A
A
D000107:Acetylation; D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000032:analysis; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002241:Carbohydrates / Q000032:analysis; D055598:Chemical Phenomena; D002621:Chemistry; D002627:Chemistry, Physical; D006595:Hexosamines / Q000032:analysis; D007306:Insecticides; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000032:analysis; D013058:Mass Spectrometry; D000432:Methanol; D008968:Molecular Conformation; D015394:Molecular Structure
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002241:Carbohydrates; D006595:Hexosamines; D007306:Insecticides; D018942:Macrolides; C001946:vancosamine; C039610:aculeximycin; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene; D008358:Mannose; D000432:Methanol