Stepwise synthesis of 2,3-O-dipalmitoyl-D-glyceric acid and an in vitro evaluation of its cytotoxicity.
2,3-O-Dipalmitoyl-D-glyceric acid (PA2-DGA) was synthesized from D-glyceric acid calcium salt and palmitoyl chloride with improved yield. Direct condensation between the D-glyceric acid calcium salt and palmitoyl chloride produced PA2-DGA with a yield of <10%, whereas stepwise synthesis yielded this compound at up to 24% of overall yield. PA2-DGA was then subjected to a cytotoxic test using normal human dermal fibroblasts and primary normal human dermal microvascular endothelial cells. This compound had no toxic effects on human cells in vitro at concentrations up to 34 µM.
Research Institute for Innovation in Sustainable Chemistry, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki, Japan.
Shun
S
Sato
Hiroshi
H
Habe
Tokuma
T
Fukuoka
Dai
D
Kitamoto
Keiji
K
Sakaki
D002118:Calcium / Q000737:chemistry; D004305:Dose-Response Relationship, Drug; D042783:Endothelial Cells / Q000166:cytology / Q000187:drug effects; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D005988:Glyceric Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005990:Glycerol / Q000737:chemistry; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008833:Microcirculation; D008956:Models, Chemical; D010168:Palmitates / Q000138:chemical synthesis* / Q000494:pharmacology*; D019308:Palmitic Acid / Q000737:chemistry; D012867:Skin / Q000473:pathology; D013997:Time Factors
D005988:Glyceric Acids; D010168:Palmitates; C073582:2,3-dipalmitoylglyceric acid; D019308:Palmitic Acid; C042971:glyceric acid; D005990:Glycerol; D002118:Calcium