Identification of molecular species of various N-acylated bacteriohopanehexol-mannosamides from the thermophilic bacterium Alicyclobacillus acidoterrestris by semipreparative HPLC and by RP-HPLC with ESI is described. We used triple-quadrupole type mass spectrometer, 1H and 13C NMR for analyzing this complex lipid. CD spectra of two compounds (model compound -7-deoxy-D: -glycero-D: -allo-heptitol obtained by stereospecific synthesis, and an isolated derivative of hopane) were also measured and the absolute configuration of both compounds was determined. On the basis of all the above methods, we identified the full structure of a new class of bacteriohopanes, represented by various N-acylated bacteriohopanehexol-mannosamides

circular dichroism, Alicyclobacillus acidoterrestris, negative RP-HPLC-ESI-MS/MS, N-acylated bacteriohopanehexol-mannosamides, ω-cyclohexyl fatty acids

NCBI PubMed ID: 20960068
Publication DOI: 10.1007/s11745-010-3482-4
Journal NLM ID: 0060450
Publisher: American Oil Chemists' Society
Correspondence: rezankabiomed.cas.cz
Institutions: Institute of Microbiology, Academy of Sciences of the Czech Republic, Prague, Czech, Department of Fermentation Chemistry and Bioengineering, Institute of Chemical Technology Prague, Prague, Czech
Methods: 13C NMR, 1H NMR, periodate oxidation, NMR-2D, TLC, ESI-MS/MS, HPLC, extraction, optical rotation measurement, acetylation, CD, reduction, cell growth, derivatization, evaporation, HILIC, HR-FAB-MS
 

• Compound ID: 14169
  

  LIP-(1-2)-a-D-ManpN-(1-35)-Subst Subst = SMILES C[C@H]([C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O)[C@@H](O){35}CO)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]5(C)[C@@H]2CC[C@@H]4[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@]45C

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  Structure type: monomer
  Compound class: glycolipid
  
   
  
  Alicyclobacillus acidoterrestris CCM 4660
  CSDB ID 47425 (all data & tools)
• Compound ID: 14170
  

  LIP-(1-2)-a-D-ManpN3Ac4Ac6Ac-(1-35)-Subst30Ac31Ac32Ac33Ac34Ac Subst = SMILES C[C@H]({30}[C@@H](O){31}[C@@H](O){32}[C@@H](O){33}[C@@H](O){34}[C@@H](O){35}CO)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]5(C)[C@@H]2CC[C@@H]4[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@]45C

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  Structure type: monomer ; 1298-1494
  Compound class: glycolipid
  
   
  
  Alicyclobacillus acidoterrestris CCM 4660
  CSDB ID 47426 (all data & tools)