Abstract
In this work, comparative experiments were explored to investigate the substrate specificity of Pseudomonas cepacia lipase in regioselective acylation of nucleosides carrying various substituents (such as the H, F, Cl, Br, I) at 2'- and 5-positions. Experimental data indicated that the catalytic performance of the enzyme depended very much on the halo-substituents in nucleosides. The increased bulk of 2'-substituents in ribose moiety of the nucleoside might contribute to the improved 3'-regioselectivity (90-98%, nucleosides a-d) in enzymatic decanoylation, while the enhancement of regioselectivity (93-99%) in 3'-O-acylated nucleosides e-h could be attributable to the increasing hydrophobicity of the halogen atoms at 5-positions. With regard to the chain-length selectivity, P. cepacia lipase displayed the highest 3'-regioselectivity toward the longer chain (C14) as compared to shorter (C6 and C10) ones. The position, orientation and property of the substituent, specific structure of the lipase's active site, and acyl structure could account for the diverse results.
References
May 1, 1976·Journal of Medicinal Chemistry·E K HamamuraJ G Moffatt
Jan 1, 1989·Journal of Medicinal Chemistry·J YamashitaM Yasumoto
Feb 15, 1997·Structure·K K KimS W Suh
Aug 28, 1998·Chemistry and Physics of Lipids·J PleissR D Schmid
Oct 25, 2001·The Journal of Organic Chemistry·W. Victor Tuomi, Romas J. Kazlauskas
Dec 26, 2001·Chemical Reviews·M Ferrero, V Gotor
Feb 18, 2004·Cancer Science·Akira Matsuda, Takuma Sasaki
Mar 24, 2004·Biochemical Pharmacology·A M BergmanG J Peters
Aug 10, 2004·Biophysical Journal·Lu YangShekhar Garde
Feb 24, 2006·Chembiochem : a European Journal of Chemical Biology·Iván LavanderaVicente Gotor
Oct 17, 2007·Journal of Agricultural and Food Chemistry·Latifa ChebilMohamed Ghoul
Jul 1, 1987·Biotechnology and Bioengineering·C LaaneC Veeger
May 12, 2009·Journal of Biotechnology·Ning LiDing Ma
Jun 23, 2009·Journal of Biotechnology·Ning LiMin-Hua Zong
Aug 22, 2009·Bioresource Technology·Rong-Ling YangMin-Hua Zong
Feb 9, 2010·Biotechnology Advances·Ning LiMin-Hua Zong
Feb 25, 2010·Biochimie·Vineet KumarSanjay V Malhotra
Jun 29, 2010·Biotechnology Advances·Tianwei TanFang Wang
Aug 18, 2010·Bioresource Technology·Shaotao PanYun Liu
Sep 3, 2010·Annual Review of Pharmacology and Toxicology·Erik De Clercq
Apr 1, 2011·The Journal of Organic Chemistry·Annika TräffJan-E Bäckvall
Jun 22, 2011·Chemical Society Reviews·Javier González-SabínFrancisca Rebolledo
Aug 9, 2011·Applied Biochemistry and Biotechnology·Zhao-Yu WangMin-Hua Zong
Sep 8, 2011·Biotechnology Letters·Zhao-Yu WangMin-Hua Zong
Sep 22, 2011·Journal of Biotechnology·Bidouil ChristelleHumeau Catherine
Mar 20, 2012·Bioresource Technology·Andrés IllanesGuillermo R Castro
Jan 23, 2013·Journal of Biotechnology·Wen-Li GaoMin-Hua Zong
Mar 22, 2013·Chemical Society Reviews·Marion B Ansorge-Schumacher, Oliver Thum
Aug 21, 2013·Biotechnology Advances·Panagiota-Yiolanda StergiouEmmanuel M Papamichael
Sep 17, 2013·Chemistry : a European Journal·Madeleine C WarnerJan-E Bäckvall
Aug 2, 2014·Applied Biochemistry and Biotechnology·Yan-Hong BiMin-Hua Zong
Citations
Apr 30, 2016·Applied Biochemistry and Biotechnology·Zhao-Yu WangJian-Bo Jia
Sep 27, 2016·BioMed Research International·Zhaoyu WangJianbo Jia
Jun 27, 2019·BioMed Research International·Yanhong BiJiali Yang
Jun 18, 2020·Frontiers in Bioengineering and Biotechnology·Yanhong BiZhengyu Jin
Oct 13, 2021·Nucleosides, Nucleotides & Nucleic Acids·Amarendra Mohan KhanRajesh Kumar