A Novel Method of Preparing Lipamino Acids and Lipopeptides

­Reference #: 01107

The University of South Carolina is offering licensing opportunities for a single-pot, one-step process for synthesizing high yields of lipoamino acids and lipopeptides. These compounds exhibit antimicrobial activity that is useful in a wide range of applications such as pharmaceuticals and cosmetics.

Invention Description:

The subject invention is a method of synthetically producing high yields of lipamino acids and lipopeptides by combining a mixture of reactants, unlike conventional methods of production that require two steps or rely on isolating lipopeptides from bacterial colonies.

Advantages and Benefits:

Compared to Schotten–Baumann reactions for synthesizing amides from amines and acid chlorides, this technology is more cost-efficient as it is enabled by relatively inexpensive precursors. Other competitive advantages include:

·       Direct synthesis of the component compounds and

·       Ability to be tuned to provide high yields of desired products.

Potential Applications:

These compounds have a variety of applications in the pharmaceutical, cosmetic, and food industries due to the unique properties contained within a single compound.

Background:

Lipopeptides are particularly effective against multiple drug resistant bacteria. For example:

·       Daptomycin and similar lipopeptides are being used against many bacterial infections including Methicillin-resistent Staphlococcus Aureus (MSRA) and several other antibiotic-resistant bacterial strains;

·       Caspofungin, a cyclic lipopolypeptide, is being used against fungal infections while caspofungin inhibits fungal cell wall formation;

·        And viscosin helps to control pathogenic membrane-enveloped viruses.

In addition, lipopeptides are often used as an ingredient in dermatological cosmetics, cleansing agents and anti-aging creams because of their low cytotoxicity and high surfactant activity. Furthermore, the food industry has made use of lipopeptides as emulsifying agents for fats, antibacterial bio-preservatives, and producing superior food textures.