Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities.

Alkylglycerols (AKGs) are bioactive natural compounds that vary by alkyl chain length and degree of unsaturation, and their absolute configuration is 2. Three AKGs (-) were synthesised in enantiomerically pure form, and were characterised for the first time together with 12 other known and naturally occurring AKGs (-, ). Their structures were established using H and C APT NMR with 2D-NMR, ESI-MS or HRESI-MS and optical rotation data, and they were tested for their antibacterial and antibiofilm activities. AKGs - and showed activity against five clinical isolates and ATCC 15442, with MIC values in the range of 15-125 µg/mL. In addition, at half of the MIC, most of the AKGs reduced biofilm formation in the range of 23%-99% and ATCC 15442 biofilm formation in the range of 14%-64%. The antibiofilm activity of the AKGs assessed in this work had not previously been studied.