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Synthesis 2019; 51(02): 477-485
DOI: 10.1055/s-0037-1610281
paper
© Georg Thieme Verlag Stuttgart · New York

Synthetic Versatility of Lipases: Application for Si–O Bond Formation and Cleavage

Patrícia Bulegon Brondani*
a   Departamento de Ciências Exatas e Educação, Universidade Federal de Santa Catarina, Blumenau, SC, 89036-256, Brazil   Email: patyqmc@gmail.com
,
Mateus Mittersteiner 
b   Departamento de Química, Universidade Regional de Blumenau, Blumenau, SC, 89019-917, Brazil
,
Morgana Aline Voigt
a   Departamento de Ciências Exatas e Educação, Universidade Federal de Santa Catarina, Blumenau, SC, 89036-256, Brazil   Email: patyqmc@gmail.com
,
Bruna Heloisa Klinkowski
b   Departamento de Química, Universidade Regional de Blumenau, Blumenau, SC, 89019-917, Brazil
,
Dilamara Riva Scharf
b   Departamento de Química, Universidade Regional de Blumenau, Blumenau, SC, 89019-917, Brazil
,
Paulo Cesar de Jesus
b   Departamento de Química, Universidade Regional de Blumenau, Blumenau, SC, 89019-917, Brazil
› Author AffiliationsCNPq (447110/2014-4) awarded to P.B.B.
Further Information

Publication History

Received: 30 July 2018

Accepted after revision: 22 August 2018

Publication Date:
21 September 2018 (online)

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Abstract

Several commercially available lipases were examined in a study on O–Si bond formation and cleavage applying silicon-based protecting groups and alcohols or the corresponding silyl ethers. With regard to deprotection, from silyl ether to the corresponding alcohol, only the solvent and the lipase were necessary. The influence of the protecting group, the lipase source, and the substituent was investigated to optimize the results. The TMS moiety could be removed in 24 hours of reaction at room temperature in aqueous systems (conv. up to 99%, depending on the substrate and lipase). The reverse reactions, that is, with the protection of the alcohols, were carried out in hexane using different silyl chlorides. The TMS, TES, and TBS moieties were successfully inserted in the primary and secondary alcohols without the need for dry conditions or an inert atmosphere, presenting conversions of up to 99%, depending on the substrate.

Key words

biocatalysis - lipases - silyl ethers - alcohol protection - alcohol deprotection

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610281.
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