110691-65-1

Basic information

• Product Name: (+)-Salsolidine hydrochloride
• Synonyms: (+)-Salsolidine hydrochloride
• CAS NO: 110691-65-1
• Molecular Weight: 243.733
• Mol File: 110691-65-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-Salsolidine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Salsolidine hydrochloride(110691-65-1)
• EPA Substance Registry System: (+)-Salsolidine hydrochloride(110691-65-1)

Safety Data

• Hazardous Substances Data: 110691-65-1(Hazardous Substances Data)

Upstream product

• 4721-98-6 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline 

Relevant articles and documents

Stereoselectivity and Structural Characterization of an Imine Reductase (IRED) from Amycolatopsis orientalis

The imine reductase AoIRED from Amycolatopsis orientalis (Uniprot R4SNK4) catalyzes the NADPH-dependent reduction of a wide range of prochiral imines and iminium ions, predominantly with (S)-selectivity and with ee's of up to >99%. AoIRED displays up to 100-fold greater catalytic efficiency for 2-methyl-1-pyrroline (2MPN) compared to other IREDs, such as the enzyme from Streptomyces sp. GF3546, which also exhibits (S)-selectivity, and thus, AoIRED is an interesting candidate for preparative synthesis. AoIRED exhibits unusual catalytic properties, with inversion of stereoselectivity observed between structurally similar substrates, and also, in the case of 1-methyl-3,4-dihydroisoquinoline, for the same substrate, dependent on the age of the enzyme after purification. The structure of AoIRED has been determined in an "open" apo-form, revealing a canonical dimeric IRED fold in which the active site is formed between the N- and C-terminal domains of participating monomers. Co-crystallization with NADPH gave a "closed" form in complex with the cofactor, in which a relative closure of domains, and associated loop movements, has resulted in a much smaller active site. A ternary complex was also obtained by cocrystallization with NADPH and 1-methyl-1,2,3,4-tetrahydroisoquinoline [(MTQ], and it reveals a binding site for the (R)-amine product, which places the chiral carbon within 4 ? of the putative location of the C4 atom of NADPH that delivers hydride to the C? -N bond of the substrate. The ternary complex has permitted structure-informed mutation of the active site, resulting in mutants including Y179A, Y179F, and N241A, of altered activity and stereoselectivity.