Reductive alkylation of lipase: experimental and molecular modeling approaches
Candida rugosa lipase was modified via reductive alkylation to increase its hydrophobicity to work better in organic solvents. The free amino group of lysines was alkylated using propionaldehyde with different degrees of modification obtained (49 and 86%). Far-ultraviolet circular dichroism (CD) spe...
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| Format: | Article |
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2004
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| author | Rahman, R.N.Z.A. Salleh, A.B. Siahaan, T.J. Zain, Sharifuddin Md Khan, F. Rahman, M.B.A. Basri, M. Tejo, B.A. |
| author_facet | Rahman, R.N.Z.A. Salleh, A.B. Siahaan, T.J. Zain, Sharifuddin Md Khan, F. Rahman, M.B.A. Basri, M. Tejo, B.A. |
| author_sort | Rahman, R.N.Z.A. |
| collection | UM |
| description | Candida rugosa lipase was modified via reductive alkylation to increase its hydrophobicity to work better in organic solvents. The free amino group of lysines was alkylated using propionaldehyde with different degrees of modification obtained (49 and 86%). Far-ultraviolet circular dichroism (CD) spectroscopy of the lipase in aqueous solvent showed that such chemical modifications at the enzyme surface caused a loss in secondary and tertiary structure that is attributed to the enzyme unfolding. Using molecular modeling, we propose that in an aqueous environment the loss in protein structure of the modified lipase is owing to disruption of stabilizing salt bridges, particularly of surface lysines. Indeed, molecular modeling and simulation of a salt bridge formed by Lys-75 to Asp-79, in a nonpolar environment, suggests the adoption of a more flexible alkylated lysine that may explain higher lipase activity in organic solvents on alkylation. |
| first_indexed | 2024-03-06T05:15:26Z |
| format | Article |
| id | um.eprints-5850 |
| institution | Universiti Malaya |
| last_indexed | 2024-03-06T05:15:26Z |
| publishDate | 2004 |
| record_format | dspace |
| spelling | um.eprints-58502019-10-25T08:56:56Z http://eprints.um.edu.my/5850/ Reductive alkylation of lipase: experimental and molecular modeling approaches Rahman, R.N.Z.A. Salleh, A.B. Siahaan, T.J. Zain, Sharifuddin Md Khan, F. Rahman, M.B.A. Basri, M. Tejo, B.A. QD Chemistry Candida rugosa lipase was modified via reductive alkylation to increase its hydrophobicity to work better in organic solvents. The free amino group of lysines was alkylated using propionaldehyde with different degrees of modification obtained (49 and 86%). Far-ultraviolet circular dichroism (CD) spectroscopy of the lipase in aqueous solvent showed that such chemical modifications at the enzyme surface caused a loss in secondary and tertiary structure that is attributed to the enzyme unfolding. Using molecular modeling, we propose that in an aqueous environment the loss in protein structure of the modified lipase is owing to disruption of stabilizing salt bridges, particularly of surface lysines. Indeed, molecular modeling and simulation of a salt bridge formed by Lys-75 to Asp-79, in a nonpolar environment, suggests the adoption of a more flexible alkylated lysine that may explain higher lipase activity in organic solvents on alkylation. 2004 Article PeerReviewed Rahman, R.N.Z.A. and Salleh, A.B. and Siahaan, T.J. and Zain, Sharifuddin Md and Khan, F. and Rahman, M.B.A. and Basri, M. and Tejo, B.A. (2004) Reductive alkylation of lipase: experimental and molecular modeling approaches. Applied Biochemistry and Biotechnology - Part A Enzyme Engineering and Biotechnology, 118 (1-3). pp. 11-20. ISSN 02732289, http://www.scopus.com/inward/record.url?eid=2-s2.0-4344684591&partnerID=40&md5=eaa7316f4dcf1404d26a1ee93a5b2340 |
| spellingShingle | QD Chemistry Rahman, R.N.Z.A. Salleh, A.B. Siahaan, T.J. Zain, Sharifuddin Md Khan, F. Rahman, M.B.A. Basri, M. Tejo, B.A. Reductive alkylation of lipase: experimental and molecular modeling approaches |
| title | Reductive alkylation of lipase: experimental and molecular modeling approaches |
| title_full | Reductive alkylation of lipase: experimental and molecular modeling approaches |
| title_fullStr | Reductive alkylation of lipase: experimental and molecular modeling approaches |
| title_full_unstemmed | Reductive alkylation of lipase: experimental and molecular modeling approaches |
| title_short | Reductive alkylation of lipase: experimental and molecular modeling approaches |
| title_sort | reductive alkylation of lipase experimental and molecular modeling approaches |
| topic | QD Chemistry |
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