Enhanced Sophorolipid Derivatives

A method for producing a cationic sophorolipid (SLP) derivative, the method comprising

• a) obtaining a lactonic SLP molecule;
• b) reducing the lactone bond into an aldehyde by applying an ate complex, lithium tri-tertbutoxyaluminum hydride (LTBA), lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA), or diisobutylaluminum hydride and n-butyllithium ate complex, thereby producing an aqueous crude linear SLP aldehyde;
• and
• e) extracting the linear SLP aldehyde from the aqueous crude linear SLP aldehyde and subjecting the extracted linear SLP aldehyde to reductive amination, thereby producing a SLP scaffold covalently linked to a primary amine, said linked SLP scaffold and primary amine comprising the cationic SLP derivative, wherein the cationic SLP derivative is present in a reductive amination reaction mixture, and purifying the cationic SLP derivative from the reductive amination mixture.

A method for producing a cationic sophorolipid (SLP) derivative, the method comprising

• a) obtaining a purified linear SLP molecule having an 18-carbon fatty acid moiety with a single unsaturated bond at the ninth carbon, and one of b) or c):
• b) using a coupling agent, installing an amide comprising one or more cationic amino acid functional groups to the carboxylic acid tail of the linear SLP molecule to produce a long-chain amide;
• or
• c) using oxidative cleavage to produce a carboxylic acid tail truncated at the ninth position, and, using a coupling agent, installing an amide comprising one or more cationic amino acid functional groups to the truncated carboxylic acid tail to produce a short-chain amide.

A sophorolipid derivative having the following structure:

• wherein R1 is H or Ac, and
• wherein R2 is a), b), c), d) or e):
• wherein R3=an alkyl or aryl group containing one or more cationic amines derived from arginine, lysine, histidine and/or glycine amino acids, and
• wherein n=1, 2, 3 or 4.