Development of biocatalytic routes to silicone-sugar conjugates, silicone polyesters and silicone polyamides

In one example, pure organosilicon-sugar conjugates were prepared in a one-step reaction, without protection-deprotection steps (Sahoo et al, 2005). This simplification of an otherwise tedious reaction that would require protection-deprotection steps was a result of the inherent regioselectivity and mild conditions of lipase catalyzed biocatalytic chemistry. The lipase-catalyzed reactions did not require activation of acid groups. Furthermore, this work established that, in comparison to organic materials, hydrophobic organosilicones were good substrates. Given the proficiency of lipases to perform selective reactions while maintaining the integrity of siloxane bonds, this discovery creates a wide-range of opportunities to use biocatalytic chemistry for the preparation of various organosilicon carbohydrates with a diversified set of functional groups to create new materials such as fibers, films, coatings, gels, and surfactants with novel properties.

Scheme 9. Lipase-catalyzed esterification between α,β-ethylglucoside and diacid-terminated siloxanes (PDMS Diacids) where x = 0, 7, and 65

References

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