Diastereoselective synthesis of aminobacteriohopanetetrol, a biomarker for methanotrophic bacteria: confirmation of the absolute configuration.
A short and convenient strategy was developed for the first stereoselective chemical synthesis of aminobacteriohopanetetrol (= (1R,2R,3S,4S)-5-amino-1-[(22R)-hopan-30-yl]pentane-1,2,3,4-tetrol; 1), a typical biomarker for methanotrophic bacteria. Comparison of the NMR spectra of the synthetic and natural (peracetylated) product enabled us to unambiguously corroborate the absolute configuration of the functionalized pentyl side chain of 1.
Pan
Weidong
W
University of Namur (FUNDP), Département de Chimie, Laboratoire de Chimie Bio-Organique, 61 rue de Bruxelles, B-5000 Namur.
Zhang
Yongmin
Y
Liang
Guangyi
G
Rohmer
Michel
M
Sinaÿ
Pierre
P
Vincent
Stéphane P
SP
D015415:Biomarkers / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008772:Methylococcaceae / Q000378:metabolism*; D008968:Molecular Conformation; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry
C524278:5-amino-1-(hopan-30-yl)pentane-1,2,3,4-tetrol; D015415:Biomarkers; D014315:Triterpenes