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Synthesis and characteristics of polydepsipeptide with pendant thiol groups
Authors:Tatsuro Ouchi  Hidenori Seike  Tatsuya Nozaki  Yuichi Ohya
Abstract:
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
Keywords:biodegradability  oligo[(glycolic acid)-alt-(L-cysteine)]  poly[(lactic acid)-depsipeptide]  ring-opening polymerization  pendant thiol group
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