Synthesis and characteristics of polydepsipeptide with pendant thiol groups

• Published in: Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 1998-06, Vol.36 (8), p.1283-1290
• Main Authors: Ouchi, Tatsuro, Seike, Hidenori, Nozaki, Tatsuya, Ohya, Yuichi
• Format: Article
• Language: English
• Subjects: Amino acids; Aminoacid polymers; Applied sciences; biodegradability; Biodegradation; Carboxylic acids; Copolymerization; Exact sciences and technology; oligo[(glycolic acid)-alt-(L-cysteine)]; Oligomers; pendant thiol group; Physicochemistry of polymers; poly[(lactic acid)-depsipeptide]; Ring opening polymerization; Solubility; Sulfur compounds; Synthesis (chemical); Synthetic biopolymers; Terpolymers
• ISSN: 0887-624X; 1099-0518
• DOI: 10.1002/(SICI)1099-0518(199806)36:8<1283::AID-POLA11>3.0.CO;2-2

To obtain water‐soluble oligodepsipeptide with pendant thiol groups, the alternating co‐oligomer [oligo(Glc‐alt‐Cys)], consisting of glycolic acid (Glc) and L‐cysteine (Cys) residues as α‐hydroxy acid and α‐amino acid residues, respectively, was prepared by means of ring‐opening homo‐oligomerization of cyclo[Glc‐Cys(MBzl)] and subsequent deprotection of methoxybenzyl groups. Moreover, to modify the properties of poly(lactic acid) [poly(LA)] and to introduce pendant thiol groups to poly(LA), the terpolymer of LA, Glc, and Cys {poly[LA‐(Glc‐Cys)]} was synthesized through ring‐opening and copolymerization of L‐lactide with the protected cyclodepsipeptide, cyclo[Glc‐Cys(MBzl)] and subsequent deprotection of methoxybenzyl groups. By changing the mol fraction of (Glc‐Cys) unit, the solubility, thermal transition, degradation behavior of the modified poly(LA), and the water contact angle of its film could be varied. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 1283–1290, 1998