高等学校化学学报 ›› 2003, Vol. 24 ›› Issue (10): 1806.

• 论文 • 上一篇    下一篇

棉子糖乙烯酯的酶催化选择性合成研究

吴起, 吕德水, 陈志春, 俞国华, 林贤福   

  1. 浙江大学化学系, 杭州 310027
  • 收稿日期:2002-09-02 出版日期:2003-10-24 发布日期:2003-10-24
  • 通讯作者: 林贤福(1963年出生),男,博士,教授,博士生导师,从事酶促合成和酶固定化方面的研究.E-mail:llc123@css.zju.edu.cn E-mail:llc123@css.zju.edu.cn
  • 基金资助:

    浙江省科技厅攻关项目(批准号:021101046)资助

Enzyme-catalyzed Regioselective Synthesis of Novel Raffinose Vinyl Esters

WU Qi, Lü De-Shui, CHEN Zhi-Chun, YU Guo-Hua, LIN Xian-Fu   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310027, China
  • Received:2002-09-02 Online:2003-10-24 Published:2003-10-24

摘要: 研究了无水吡啶中酶催化棉子糖和丁二酸二乙烯酯、己二酸二乙烯酯、癸二酸二乙烯酯的酯交换反应,高选择性地合成了3种具有不同链长的可聚合的棉子糖乙烯酯.化合物经1HNMR,13CNMR和2DNMR表征,确证主要在棉子糖的β-呋喃果糖残基的C-1位OH上酯化.考察了7种不同来源的酶催化棉子糖酯合成的活性及温度、时间对反应的影响.

关键词: 棉子糖, 乙烯酯, 酶催化合成, 酯交换反应

Abstract: Sugar esters have recently received increased attention from the viewpoint of renewable resources.Specifically vinyl esters from carbohydrates by enzyme-catalyzed regioselective transformations offer a new family of functional water-soluble monomers for preparation of sugar-based polymers.Here we reported enzyme-catalyzed regioselective synthesis of novel polymerizable raffinose vinyl ester.Transesterification of raffinose with divinyl succinate, divinyl adipate and divinyl sebacate in anhydrous pyridine at 50℃ for6d was catalyzed by an alkaline protease from Bacillus subtilis.Three raffinose vinyl esters with different acyl donor chain lengths were regioselectively synthesized at 55%, 48% and 30% yields, respectively.Characterization of the products by 1HNMR, 13CNMR, and 1H-1Hcorrelation spectroscopy and 1H-13C heteronuclear multiple quantum coherence NMR revealed that the ester was substituted at C-1 position of β-fructofuranose moiety in raffinose.Reaction conditions for the esterification were investigated.Activities of seven commercial enzymes from different sources catalyzing synthesis of raffinose ester were compared.Lipase from porcine pancreas(PPL) and alkaline protease from Bacillus subtilis had high activities.We also studied the effect of temperature and incubation time on raffinose esters synthesis catalyzed by alkaline protease from Bacillus subtilis and found the optimal temperature and reaction time were 50℃ and 6d respectively.

Key words: Raffinose, Vinyl ester, Enzyme catalyzed synthesis, Transesterification

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