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D-Excess-LaA Production Directly from Biomass by Trivalent Yttrium Species: Mechanism and Enantioselectivity

116 Pages Posted: 18 Jan 2019 Sneak Peek Status: Published

See all articles by Shuguang Xu

Shuguang Xu

Sichuan University - Key Laboratory of Green Chemistry and Technology

Jing Li

Sichuan University - Key Laboratory of Green Chemistry and Technology

Jianmei Li

Sichuan University - Key Laboratory of Green Chemistry and Technology

Yi Wu

Sichuan University - Key Laboratory of Green Chemistry and Technology

Yuan Xiao

Sichuan University - Key Laboratory of Green Chemistry and Technology

Changwei Hu

Sichuan University - Key Laboratory of Green Chemistry and Technology

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Abstract

D-Lactic acid (D-LaA) synthesis directly from actual biomass via chemocatalytic conversion has shown high potential for satisfying its enormous demand in widespread applications. Here we report yttrium (Y(III)) species catalyzed conversion of xylose and raw lignocelluloses to LaA with the highest yield of 87.3% (20% ee to D-LaA). Combining experiments with theoretical modelling, we reveal that [Y(OH)2(H2O)2]+ is the possible catalytically active species, enabling the unconventional cleavage of C3-C4 in xylulose and the subsequent dehydration of glyceraldehyde to pyruvaldehyde (PRA). The distinct interactions between hydrated-PRA and [Y(OH)2(H2O)2]+ species contribute to the formation of different enantiomers, wherein H-migration via re-face attack leads to L-LaA and that via si-face attack yields D-LaA. The lower strain energy barrier is the origin of excess D-enantiomer formation.

Suggested Citation

Xu, Shuguang and Li, Jing and Li, Jianmei and Wu, Yi and Xiao, Yuan and Hu, Changwei, D-Excess-LaA Production Directly from Biomass by Trivalent Yttrium Species: Mechanism and Enantioselectivity (November 2, 2018). Available at SSRN: https://ssrn.com/abstract=3277363 or http://dx.doi.org/10.2139/ssrn.3277363
This is a paper under consideration at Cell Press and has not been peer-reviewed.

Shuguang Xu

Sichuan University - Key Laboratory of Green Chemistry and Technology

Chengdu, Sichuan 610064
China

Jing Li

Sichuan University - Key Laboratory of Green Chemistry and Technology

Chengdu, Sichuan 610064
China

Jianmei Li

Sichuan University - Key Laboratory of Green Chemistry and Technology

Chengdu, Sichuan 610064
China

Yi Wu

Sichuan University - Key Laboratory of Green Chemistry and Technology

Chengdu, Sichuan 610064
China

Yuan Xiao

Sichuan University - Key Laboratory of Green Chemistry and Technology

Chengdu, Sichuan 610064
China

Changwei Hu (Contact Author)

Sichuan University - Key Laboratory of Green Chemistry and Technology ( email )

Chengdu, Sichuan 610064
China

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