✦ LIBER ✦

Synthesis of 3-O-acyl esters of serine and threonine

✍ Scribed by Guido V. Marinetti

Publisher: Elsevier Science
Year: 1983
Tongue: English
Weight: 398 KB
Volume: 33
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(83)90018-x

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✦ Synopsis

The 3-O-acyl derivatives of serine and threonine have been prepared by reacting oleoyl chloride and palmitoyl chloride with N-t-butoxycarbonyl (N-T-BOC) serine and N-t-BOC threonine. The t-BOC group was removed by treatment with 4 N HCI in dioxane. The products were identified by proton magnetic resonance spectroscopy, infrared spectroscopy, elemental analysis and chromatographic properties. The O-acyl serines and O-acyl threonines were converted to their methyl esters by treatment with boron trifluoride in methanol and were converted to their dinitrophyl derivatives by treatment with dinitrofluorobenzene (DNFB). The yield of the dinitrophenyl derivatives was very high but the yield of methyl esters was low due mainly to methanolysis and loss of the fatty acyl group. The O-acyl serines and O-acyl threonines prepared will provide standards for researchers who are interested in identifying fatty acids esterified to serine and threonine hydroxyl groups in membrane proteins.

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