A Novel Synthesis of N-Alkoxycarbonyl Amino Acids and Surfactant Properties of Their Sodium Salts

Abstract

N-Acyl amino acids have been prepared from fatty acid chlorides and amino acids, but it may not be easy to vary the hydrophobic groups on the view point of availability. In this work, instead of acid halides, long alkyl chloroformates were prepared by the facile reaction of alcohols and triphosgene as an induction agent of hydrophobic group on amino acids. N-Alkoxycarbonyl amino acids were synthesized from alkyl chloroformate and amino acids under Schötten-Baumann reaction condition with some modification. Surfactant properties of their sodium salts were studied by surface tension measurements, dynamic light scattering and foaming test, and compared with those of N-acyl amino acids. Sodium salts of N-alkoxycarbonyl amino acids showed an excellent surface tension lowering ability comparable to N-acyl amino acids, and they also exhibited good foaming ability and stability.

A releasable disulfide carbonate linker for polyethyleneimine (PEI)-based gene vectors

“…1, PEI-SS-CLs were synthesized by the crosslinking reaction between PEI 2k and a reducible crosslinker 2. Bichloroformate 2 was prepared using triphosgene and compound 1 directly at a molar ratio of 1 : 3 at 0 1C 34,35 and precipitated from the solution of CH 2 Cl 2 -hexane without further purification. Chloroformate can readily react with amines of PEI 2k at 0-5 1C and formed carbamate linkages.…”

“…This thiol-specific cleavable disulfide bond was reported to cleave in the intracellular environment followed by selfintramolecular cyclization. 33,34 Decomplexation of pDNA from polyplexes was triggered by DTT and heparin, mimicking the reduced intracellular environment (Fig. 3).…”

Surface and Antimicrobial Properties ofN-Palmitoyl Amino Acid–Based Surfactants

“…[1][2][3][4] Amino acid surfactants are being used in many applications like household products, personal care products, industrial applications and pharmaceuticals as cleaning, wetting, foaming, emulsifying, anti-corrosive, antibacterial, solublizing agents etc. [5][6][7] Amino acid surfactants were used for chiral isomers separation, recognition and also finds use as catalyst in many chemical reactions. [8,9] Palmitic acid-based amides of different quaternized salts were prepared and evaluated for CMC and thermodynamic properties by surface tension method and they can also be used as dispersing and petroleum collecting agents.…”

Efficient Microwave-Assisted Synthesis of Ionic Esterified Amino Acids

“…The synthesis of carboxylic esters is one of the most fundamental protocols for producing natural and synthetically useful chemicals in peptide chemistry [ 7 ]. Particularly, long alkyloyl amino acids are important compounds due to their nutritional [ 8 ] and surfactant properties [ 9 ]. Some of them also show antisickling activity [ 10 ], protective properties against microorganism growth, as well as in the preservation of perishable food products [ 11 ].…”