2018Chinese Journal of ChemistryRequires access

Biomimetic Chiral Pyridoxal and Pyridoxamine Catalysts

Jianfeng Chen, Yong Ethan Liu, Xing Gong, Limin Shi, Baoguo Zhao

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Abstract

Vitamin B6 serves as universal co‐enzymes in biological systems. However, its catalytic power has not been applied into the area of asymmetric catalysis. Based on the core structure of vitamin B6, we have developed several types of pyridoxal and pyridoxamine catalysts with different structural skeletons and different electronic properties. With these pyridoxals and pyridoxamines as catalysts, we have realized biomimetic asymmetric transamination of α‐keto acids and biomimetic asymmetric Mannich reaction of glycinate, respectively, to give various chiral α‐amino acids and α,β‐diamino acids in good yields with excellent diastero‐ and/or enantioselectivities. Both of the reactions have perfectly mimicked the corresponding biological transformations.

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What this paper is about

Vitamin B6 serves as universal co‐enzymes in biological systems. However, its catalytic power has not been applied into the area of asymmetric catalysis. Based on the core structure of vitamin B6, we have developed several types of pyridoxal and pyridoxamine catalysts with different structural skeletons and different electronic properties. With these pyridoxals and pyridoxamines as catalysts, we have realized biomimetic asymmetric transamination of α‐keto acids and biomimetic asymmetric Mannich reaction of glycinate, respectively, to give various chiral α‐amino acids and α,β‐diamino acids in good yields with excellent diastero‐ and/or enantioselectivities. Both of the reactions have perfectly mimicked the corresponding biological transformations.

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Available abstract

Vitamin B6 serves as universal co‐enzymes in biological systems. However, its catalytic power has not been applied into the area of asymmetric catalysis. Based on the core structure of vitamin B6, we have developed several types of pyridoxal and pyridoxamine catalysts with different structural skeletons and different electronic properties. With these pyridoxals and pyridoxamines as catalysts, we have realized biomimetic asymmetric transamination of α‐keto acids and biomimetic asymmetric Mannich reaction of glycinate, respectively, to give various chiral α‐amino acids and α,β‐diamino acids in good yields with excellent diastero‐ and/or enantioselectivities. Both of the reactions have perfectly mimicked the corresponding biological transformations.

Key concepts: Pyridoxamine, Chemistry, Transamination, Catalysis, Pyridoxal, Vitamin b6, Enantioselective synthesis, Amino acid

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