Enantiomers of Natural Lipids

Phospholipids in natural lipids are usually chiral and exist in enantiomers. When constructing liposomes, one can choose to use specific enantiomers to prepare artificial membrane vesicles. In this way, the enantiomers in the liposome will correspond to the enantiomers present in the natural lipid. The choice of different enantiomers may have an impact on the properties and behavior of the liposome, including membrane stability, charging properties, and interactions with other molecules, etc. BOC Sciences offers a variety of enantiomers of natural lipids, such as Ent-DSPE and Ent-DHEA.

Fig. 1. Synthesis of ent-Cholesterol (The Journal of Organic Chemistry. 2002, 67(14): 4893-4900).

What are Enantiomers of Natural Lipids?

Enantiomers of natural lipids refer to chiral isomers of natural lipid molecules with the same chemical composition and structure. However, the spatial configuration of these enantiomers is mirror symmetrical. Moreover, due to chirality, the enantiomers of natural lipids exhibit different properties in terms of biological functions, metabolism, and interactions. These different properties can be manifested in biological activities and metabolic pathways, which can affect the functions and effects of the enantiomers of natural lipids due to different interactions with enzymes, receptors or other molecules.

Examples of Enantiomers of Natural Lipids

Ent-DSPE

Ent-DSPE, with the chemical name (2S)-2,3-Diacyloxypropyl 2-(trimethylammonio)ethyl phosphate, belongs to the class of phospholipids and is a phosphatidylcholine derivative. Ent-DSPE exists in two enantiomers, which can be used in the preparation of nanoparticles and liposomes.

Ent-DHEA

Ent-DHEA, chemically known as Dehydroepiandrosterone, is endogenous steroid hormone that is synthesized in the body as a steroid precursor and exerts a variety of physiological effects. These roles include, participation in the regulation of immune function, metabolic regulation, anti-inflammatory effects and so on.

Ent-DMPC

Ent-DMPC, chemically known as (2S)-2,3-Diacyloxypropyl 2-(trimethylammonio)ethyl phosphate, is one of the enantiomers of dipalmitoylglycerophosphatidylcholine (DMPC). Ent-DMPC can be used in the construction of artificial liposomes and as one of the components of drug delivery systems, carriers and model membranes.

Factors Affecting the Enantiomers of Natural Lipids

• Synthesis Pathway. The formation of enantiomers of natural lipids can be influenced by the enzymes and enzyme systems involved in the synthesis process.
• Environmental Conditions. Factors such as temperature, solvent selection, and reaction conditions (e.g., catalyst, reaction time) may also affect enantioselectivity.
• Chiral Inducers. Chiral inducers can selectively promote or hinder enantiomer formation or separation by interacting with the reactants or separation targets.

Characteristics of Enantiomers of Natural Lipids

Physicochemical Properties

The enantiomers of natural lipids have the same chemical composition and molecules, but there are some differences in liquid crystal properties, solubility, surface activity and interactions.

Drug Metabolism and Toxicity

Some enantiomers may be more readily metabolized or cleared by the organism, while others may exhibit different toxicity or pharmacokinetic profiles.

Drug Delivery and Effects

Specific enantiomers can have an impact on the drug encapsulation, release and delivery properties of liposomes. The choice of enantiomer may modulate the stability, permeability, and charging properties of liposomes, thereby affecting drug delivery and therapeutic efficacy.

Applications of Enantiomers of Natural Lipids

Liposomal Formulations

Enantiomers of natural lipids can have an impact on the nature and properties of liposome, thus the selection of specific enantiomers may modulate the properties of liposomes for better drug delivery.

Cosmetics and Personal Care Products

Enantiomers may affect the texture, stability and permeability of a product. Therefore, the selection of appropriate enantiomers in the manufacture of cosmetics can improve the feel and effect of the product.

Agrochemicals

Enantiomers of natural lipids can be applied in pesticides and herbicides, and, the choice of enantiomers may affect the activity, selectivity of pesticides.

BOC Sciences offers many types of enantiomers of natural lipids. Our highly skilled scientists are well versed in liposome technology and can provide expert guidance and support in selecting the best enantiomers of natural lipids for a particular application.

Reference

1. Jiang, X. et al. Total synthesis of ent-cholesterol via a Steroid C, D-ring side-chain synthon. The Journal of Organic Chemistry. 2002, 67(14): 4893-4900.