Easy and Simple SiO<sub>2</sub> Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases

Mittersteiner, Mateus; Machado, Tayani M.; Jesus, Paulo Cesar de; Brondani, Patrícia B.; Scharf, Dilamara R.; Wendhausen, Renato

doi:10.21577/0103-5053.20160277

Acessibilidade / Reportar erro

Brasil

Journal of the Brazilian Chemical Society

Español English

Brasil

Español English

sumário « anterior atual seguinte »

Sumário

Articles • J. Braz. Chem. Soc. 28 (07) • July 2017 • https://doi.org/10.21577/0103-5053.20160277 copy

Easy and Simple SiO₂ Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases

Authorship SCIMAGO INSTITUTIONS RANKINGS

In this study, lipase from Candida antarctica B (Lipozyme CaLB-L) was successfully immobilized on SiO₂ through adsorption and used to obtain (R)-(+)-esters derived from (R,S)-1-phenylethanol. The new immobilized enzyme was compared with commercially immobilized lipases (Novozyme 435, Lipozyme 435 and Pseudomonas cepacia (PSC-II and PSD-I)). Lipozyme CaLB-L adsorbed onto SiO₂ was found to be a good catalyst and, under optimal conditions, esters could be obtained with conversion 44%, enantiomeric excess of product (ee_p) > 99%, enantiomeric excess of substract (ee_s) 77% and enantiomeric ratio (E) > 200. The lipase maintained enantioselectivity under adverse conditions, such as in organic solvents, with an excess of substrate and at different temperatures. The immobilized lipase could be reused five times with no significant loss of the activity.

Keywords:
lipases; immobilization; silica gel; enzymatic resolution; acylation reactions


entry	Obtained ester	Lipozyme 435^a a Reaction conditions: 1 mmol acyl acid donor, 1 mmol 1-phenylethanol, immobilized lipase (100 mg Lipozyme 435 or Novozyme 435 or 1.5 g SiO2 containing 1 mL of Lipozyme CaLB L), 25 mL of n-hexane, 37 ºC, 48 h. Enantiomeric ratio (E) > 200 in all cases, calculated using the formula E= {ln [eep(1 -ees)] / (eep + ees)} / {ln [eep(1 + ees)] / (eep + ees)}.1 c.: Conversion; eep: enantiomeric excess of product; ees: enantiomeric excess of substract.			SiO₂-CaLB-L^a a Reaction conditions: 1 mmol acyl acid donor, 1 mmol 1-phenylethanol, immobilized lipase (100 mg Lipozyme 435 or Novozyme 435 or 1.5 g SiO2 containing 1 mL of Lipozyme CaLB L), 25 mL of n-hexane, 37 ºC, 48 h. Enantiomeric ratio (E) > 200 in all cases, calculated using the formula E= {ln [eep(1 -ees)] / (eep + ees)} / {ln [eep(1 + ees)] / (eep + ees)}.1 c.: Conversion; eep: enantiomeric excess of product; ees: enantiomeric excess of substract.			Novozyme 435
entry	Obtained ester	c. / %	ee_p / %	ee_s / %	c. / %	ee_p / %	ee_s / %	c. / %	ee_p / %	ee_s / %
1	butyrate	38	> 99	68	39	> 99	65	38	> 99	63
2	pentanoate	39	> 99	70	38	> 99	70	39	> 99	65
3	hexanoate	38	> 99	65	38	> 99	70	39	> 99	64
4	heptanoate	39	> 99	67	41	> 99	70	40	> 99	65
5	octanoate	39	> 99	76	37	> 99	67	37	> 99	64
6	decanoate	39	> 99	68	38	> 99	67	37	> 99	64
7	dodecanoate	39	> 99	66	37	> 99	67	39	> 99	65

entry	Molar ratio	Lipozyme 435^a a Reaction conditions: 1 mmol butyric acid, corresponding amount of 1-phenylethanol, lipase, 25 mL n-hexane, 37 ºC, 48 h. Enantiomeric ratio (E) > 200 in all cases. c.: Conversion; eep: enantiomeric excess of product; ees: enantiomeric excess of substract.			SiO₂-CaLB-L^a a Reaction conditions: 1 mmol butyric acid, corresponding amount of 1-phenylethanol, lipase, 25 mL n-hexane, 37 ºC, 48 h. Enantiomeric ratio (E) > 200 in all cases. c.: Conversion; eep: enantiomeric excess of product; ees: enantiomeric excess of substract.
entry	Molar ratio	c. / %	ee_p / %	ee_s / %	c. / %	ee_p / %	ee_s / %
1	0.5	45	> 99	83	44	> 99	77
2	1.0	37	> 99	68	39	> 99	68
3	1.5	26	> 99	72	30	> 99	59
4	2.0	21	> 99	52	24	> 99	49

entry	Solvent	log P	Lipozyme 435^a a Reaction conditions: 1 mmol butyric acid, 1 mmol 1-phenylethanol, immobilized lipase (100 mg Lipozyme 435 or 1.5 g SiO2 containing 1 mL of Lipozyme CaLB-L), 25 mL of organic solvent, 37 ºC, 48 h. Enantiomeric ratio (E) > 200 in all cases. c.: Conversion; eep: enantiomeric excess of product; ees: enantiomeric excess of substract.			SiO₂-CaLB-L^a a Reaction conditions: 1 mmol butyric acid, 1 mmol 1-phenylethanol, immobilized lipase (100 mg Lipozyme 435 or 1.5 g SiO2 containing 1 mL of Lipozyme CaLB-L), 25 mL of organic solvent, 37 ºC, 48 h. Enantiomeric ratio (E) > 200 in all cases. c.: Conversion; eep: enantiomeric excess of product; ees: enantiomeric excess of substract.
entry	Solvent	log P	c. / %	ee_p / %	ee_s / %	c. / %	ee_p / %	ee_s / %
1	DIOX	-1.1	19	> 99	45	6	> 99	40
2	THF	0.45	6	> 99	39	6	99	4
3	DCM	1.5	12	> 99	23	8	> 99	18
4	CYHEX	3.2	40	> 99	71	45	> 99	72
5	HEX	3.5	38	> 99	68	40	> 99	68
6	HEPT	4.0	41	> 99	77	43	> 99	70
7	ISO	4.4	41	> 99	67	21	> 99	67
8	PE	5.1	40	> 99	67	20	> 99	65

Sociedade Brasileira de Química Instituto de Química - UNICAMP, Caixa Postal 6154, 13083-970 Campinas SP - Brazil, Tel./FAX.: +55 19 3521-3151 - São Paulo - SP - Brazil
E-mail: office@jbcs.sbq.org.br

Acompanhe os números deste periódico no seu leitor de RSS

[1] *e-mail: pcj@furb.br

Brasil

Brasil

Easy and Simple SiO2 Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases

Easy and Simple SiO₂ Immobilization of Lipozyme CaLB-L: Its Use as a Catalyst in Acylation Reactions and Comparison with Other Lipases