Phospholipids Synthesis

Lipid synthesis is a complex process, the stability of which is affected by a number of factors, such as the selection of phospholipids, their synthesis and modification, all of which affect the function of lipids in cellular metabolism and biology. BOC Sciences offers services for the synthesis of phospholipids, including semi-synthesis and total synthesis, and offers a wide range of phospholipid syntheses for our customers.

Synthesis of Phospholipids

In terms of phospholipid structure, the synthesis of phospholipids mainly involves the introduction of two saturated or unsaturated acyl groups (side chains) and the coupling of the polar ends of the phospholipid. Phospholipids can be synthesized using glycerol as a precursor by first protecting one of the hydroxyl groups of the glycerol, freeing the other two hydroxyl groups, and attaching two identical or different acyl groups depending on the purpose. When introducing different acyl groups, the difference in the activity of the primary and secondary hydroxyl groups can be utilized or the selective protecting group can be utilized. Finally, the protective group is removed and coupled to the phospholipid head group. The introduction of the acyl group can utilize the corresponding fatty acid or a more active acyl chloride. The coupling of the phospholipid headgroup is actually the formation of a phosphodiester, which can be accomplished either by a tetra-coordinated phosphorylating reagent or by a more reactive tri-coordinated phosphorus reagent.

Fig 1. Schematic of phospholipid synthesis. (Yao et al., 2018)

BOC Sciences' Phospholipid Synthesis Services

• Phospholipid semisynthesis

The semi-synthesis of phospholipids is the modification of phospholipids, and we typically offer chemical modification of phospholipids to our customers.

Chemical modification of phospholipids is the alteration of the structure or fatty acid composition of phospholipids to change the functional properties of phospholipids according to the requirements of different purposes. Concentrated phospholipids have a variety of functional groups which can successfully undergo hydrolysis, hydrogenation, hydroxylation, ethoxylation, halogenation, sulfonation, acetylation, succinylation, and phosphorylation reactions. Chemical modification is mainly carried out on the unsaturated double bonds and X substituents of phospholipids. The purpose of phospholipid modification is mainly to change part of the structure of the phospholipid molecule, to improve the HLB value (hydrophilicity), to increase the fluidity, permeability, to reduce the degree of unsaturation and so on.

• Total synthesis of phospholipids

The total synthesis method of phospholipids is generally used to synthesize target phospholipid compounds by using the backbone of glycerol or other compounds as a precursor, and then through the formation of phospholipid bonds after long-chain alkylation or acylation. It is characterized by relatively many synthetic steps, flexibility, and the general use of protective groups. In addition to the preparation of general basic phospholipids, other active centers can be introduced to synthesize a variety of phospholipid derivatives with optical activity and various physiological activities. It is suitable for the preparation of single phospholipids in larger quantities.

Types of Phospholipids that can be Prepared

• Phosphatidylethanolamine (PE): Ethanolamine and phosphatidic acid salts are added to the reaction solvent, and the reaction is facilitated by the addition of a certain amount of activator and catalyst.
• Phosphatidylserine (PS): The pathway for PS synthesis includes base exchange reactions of serine with ethanolamine in PE or serine with choline in PC. These exchange reactions can be catalyzed by a single enzyme, phosphatidylserine synthase 1.
• Phosphatidylcholine (PC): Phosphatidylcholine is synthesized primarily via the CDP-choline pathway. Choline is first activated by phosphorylation and then by coupling to CDP before attaching to 1,2-diacylglycerol.
• Phosphatidylinositol (PI): Synthesis of PI begins with the formation of CDP-diacylglycerol from phosphatidic acid and CTP.
• Phosphatidylglycerol (PG): Synthesis of PG begins via CDP-diacylglycerol and glycerol-3-phosphate, a reaction that produces phosphatidylglycerol phosphate. Phosphatidylglycerol phosphate is then converted to PG by removing the phosphate.

BOC Sciences offers you more than just the above, if you have other synthetic service needs, keep in touch with us and we will customize a solution just for you.