New insights on the structure of algaenan from Botryoccocus braunii race A and its hexane insoluble botryals based on multidimensional NMR spectroscopy and electrospray-mass spectrometry techniques.
Through solution state NMR spectroscopy and quadrupole-time-of-flight mass spectrometry (Q-TOF MS) studies of the hexane insoluble botryal extract of the algae Botryococcus braunii race A, coupled with high-resolution magic-angle-spinning (HR-MAS) NMR spectroscopy of the algaenan from this alga, it has been possible to advance the structural understanding of this geochemically important biopolymer. It was found that the hexane insoluble botryals in this study constitute a mixture of low molecular weight unsaturated aliphatic aldehydes and unsaturated hydrocarbons with an average chain length of about 40 carbons. Exact assignments were provided for many of the structural units present and describe the average constitution of the mixture as a whole. Reticulation of the low molecular weight chains via acetal and ester links explains the primary make up of algaenan. In this study, it is concluded that the algaenan results from the reticulation of low molecular weight hexane insoluble botryal species rather than the polyaldehyde as previously observed in studies of algae at alternate stages of their growth cycle.
Simpson
Andre J
AJ
Department of Chemistry, The Ohio State University, Columbus, OH 43210, USA. asimpson@utsc.utoronto.ca
Zang
Xu
X
Kramer
Robert
R
Hatcher
Patrick G
PG
D000447:Aldehydes / Q000737:chemistry* / Q000302:isolation & purification; D001704:Biopolymers / Q000737:chemistry* / Q000302:isolation & purification; D000460:Chlorophyta / Q000737:chemistry* / Q000145:classification; D006586:Hexanes / Q000737:chemistry; D006838:Hydrocarbons; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D008970:Molecular Weight; D019906:Nuclear Magnetic Resonance, Biomolecular / Q000379:methods; D012995:Solubility; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods
D000447:Aldehydes; D001704:Biopolymers; D006586:Hexanes; D006838:Hydrocarbons; C030011:carbene; D008697:Methane