Hello,
I've used the procedure proposed by Marrapu et al. (2015) --> Article A novel method to synthesize 1-acyl-sn-glycero-3-phosphochol...
To synthesize di-C:8, di-C:12 and di-C:18 glycero-phosphocholines, I've followed the procedure 6a-K in the reference above (with 5 eq. acyl cholrides for 1 eq. GPC for all). I've obtained my di-C:18 successfully with a yield near 100%. In contrast, I got less than 5% of di-C:8 and di-C:12 glycero-phosphocholines!Is there any researchers who faced the same problem for short chain PCs using this protocol? What could be the problem?
Thank you,
Nabil Adrar
I suggest you look into the purity level conformance of the reagents used in your study and those used by reported authors, sometimes this can be an issue in synthesis as well.
Not am not sure why shorter chain fatty acids would be more difficult than longer chain fatty acids, but in general acylation of GPC is more difficult than one would think. Our experiences are summarized in this publication: Chemoenzymatic synthesis of fluorogenic phospholipids and evaluation in assays of phospholipases A, C and D December 2016 · Chemistry and Physics of Lipids 202.
Check the reaction conditions, such as anhydrous and anaerobic. Use NMR，chromatography and other methods to check whether the impurities and whether they are the substances you need.
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