Optically active: microwave-assisted synthesis and characterization of l-lysine-derived poly (amide-imide)s

• Published in: Amino acids Vol. 41; no. 2; pp. 485 - 494
• Main Authors: Alborzi, Ali Reza, Zahmatkesh, Saeed, Zare, Karim, Sadeghi, Javad
• Format: Journal Article
• Language: English
• Published: Vienna Springer Vienna 01.07.2011; Springer Nature B.V
• Subjects: Amides - chemical synthesis; Amides - chemistry; Amino acids; Analytical Chemistry; Anhydrides; Backbone; Biochemical Engineering; Biochemistry; Biomedical and Life Sciences; Drug Stability; Halogenation; Hot Temperature; Imides - chemical synthesis; Imides - chemistry; Life Sciences; Lysine - analogs & derivatives; Lysine - chemical synthesis; Lysine - chemistry; Microwaves; Molecular Structure; Neurobiology; Optical activity; Optical Rotation; Original Article; Polymerization; Polymers; Polymers - chemical synthesis; Polymers - chemistry; Proteomics; Spectrophotometry, Infrared; Tacticity; Thermogravimetric analysis; Thermal properties; lysine; Poly (amide-imide); Optically active; Microwave-assisted polymerization
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-010-0767-0

l -lysine hydrochloride was transformed to ethyl l -lysine dihydrochloride. This salt was reacted with trimellitic anhydride to yield the corresponding diacid ( 1 ). Microwave-assisted polycondensation results a series of novel Poly (amide-imide)s ( PAI a–i ). These polymers have inherent viscosities in the range of 0.23–0.66 dl g −1 , display optical activity from +8.02 to +15.11 (as there is no obvious regioselectivity between alpha and epsilon amino groups of the chiral diacid during the polymerization step then random orientation of diacid moieties along the polymer backbone can be predicted and the concept of “tacticity” cannot be addressed in this research), and are readily soluble in polar aprotic solvents. They start to decompose ( T 10% ) above 362°C and display glass-transition temperatures at 119–153°C. All of the above polymers were fully characterized by UV, FT-IR and 1 H NMR spectroscopy, elemental analysis, thermogravimetric analyses, DSC, inherent viscosity measurement and specific rotation.