Ura Yasuyuki, Al-Sayah Mohammad, Montenegro Javier, Beierle John M, Leman Luke J, Ghadiri M Reza
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Org Biomol Chem. 2009 Jul 21;7(14):2878-84. doi: 10.1039/b903612a. Epub 2009 Jun 8.
We describe the preparation and characterization of polythioesters composed of alternating alpha-amino acid and alpha-thioglycolic acid residues that undergo dynamic constitutional exchange under mild conditions. The polymers are assembled via reversible ring-opening polymerizations of 1,4-thiazine-2,5-diones and related monomers in solution-phase conditions that do not require the use of transition metal catalysts. Because 1,4-thiazine-2,5-diones can be derived in part from alpha-amino acids, a variety of side chain functionalized monomers in optically pure forms could readily be accessed. In addition, the resulting polythioesters have the potential for intra- and inter-chain hydrogen bonding, which is known to impart materials properties to other previously studied polyamides. The studies reported here could be useful in advancing a new class of biodegradable polymers and furthermore suggest that dynamic constitutional exchange could be exploited to modify many known synthetic and natural polythioesters.
我们描述了由交替的α-氨基酸和α-巯基乙酸残基组成的聚硫酯的制备和表征，这些聚硫酯在温和条件下会发生动态结构交换。这些聚合物是通过1,4-噻嗪-2,5-二酮及相关单体在溶液相条件下的可逆开环聚合反应组装而成的，该条件无需使用过渡金属催化剂。由于1,4-噻嗪-2,5-二酮可部分衍生自α-氨基酸，因此可以很容易地获得各种光学纯形式的侧链官能化单体。此外，所得的聚硫酯具有链内和链间氢键的潜力，已知这种氢键会赋予其他先前研究的聚酰胺材料性能。此处报道的研究可能有助于推进一类新型可生物降解聚合物的发展，并且进一步表明动态结构交换可用于修饰许多已知的合成和天然聚硫酯。
