Earthworms as a Biocatalyst: In Asymmetric Aldol Reactions

Abstract

A crude extract from earthworms was used as an environmentally friendly and easily accessible biocatalyst for asymmetric direct aldol reactions. The β-hydroxy carbonyl compounds could be prepared in yields of up to 94%, with ee values of up to 98% and dr of up to >99:1. A wide range of substrates could participate in the reaction. This earthworm catalyst was also efficient in the large-scale reaction, providing product in excellent yield and good selectivity. The protocol as an example gives inspiration for the development of sustainable catalysts from nature, which also provides a potential possibility for application of earthworm catalyst in industrial production.

Development of fructose-1,6-bisphosphate aldolase enzyme peptide mimics as biocatalysts in direct asymmetric aldol reactions

“…This outcome may suggest longer reaction times are required for the formation of the product. The aforementioned solvents were selected in this study because they are readily available in the lab and they have been reported in literature, 3,45 to yield aldol products with high yields and good selectivity. Although high-boiling organic solvents such as DMSO and DMF are commonly used in aldol reactions studies they are oen considered problematic for large-scale synthesis due to inconvenient work-up, solvent removal and recovery steps.…”

Asymmetric cross-aldol reaction of isatin and ketones catalyzed by crude earthworm extract as efficient biocatalyst

“…They reported the products yields up to 51% with enantioselectivities up to 87% for the reaction. Zhang et al, (28) used earthworm extract as an environmental biocatalyst for asymmetric synthesis of various β-hydroxy carbonyl compounds in yields up to 94%, ee values of up 98% and dr values of up to 99%.…”