Literature summary for 1.21.3.3 extracted from

Resch, V.; Lechner, H.; Schrittwieser, J.H.; Wallner, S.; Gruber, K.; Macheroux, P.; Kroutil, W.
Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates (2012), Chemistry, 18, 13173-13179.

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Application

Application	Comment	Organism
synthesis	substrate tuning by introducing a fluoro moiety at one potential reactive carbon center switches the reaction to the formation of exclusively one regioisomer with perfect enantioselectivity. The formation of 11-hydroxy-functionalized tetrahydroprotoberberines instead of the commonly formed 9-hydroxy-functionalized products from 1,2,3,4-tetrahydroisoquinolines can be successfully promoted	Eschscholzia californica

Organism

Organism	UniProt	Comment	Textmining
Eschscholzia californica	P30986	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
1-(2-fluoro-3-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol + O2	-	Eschscholzia californica	(13aS)-12-fluoro-3-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,11-diol + H2O	49% conversion, more than 99% of product (13aS)-12-fluoro-3-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-2,11-diol	?
1-(2-fluoro-3-hydroxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol + O2	-	Eschscholzia californica	(13aS)-12-fluoro-2-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,11-diol + H2O	49% conversion, more than 99% of product (13aS)-12-fluoro-2-methoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,11-diol	?
1-(3-hydroxy-4-methoxybenzyl)-7-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ol + O2	-	Eschscholzia californica	(13aS)-2,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,9-diol + isocoreximine + H2O2	53% conversion, ratio (13aS)-2,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinoline-3,9-diol to isocoreximine is 98:2	?
3-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-fluorophenol + O2	-	Eschscholzia californica	(13aS)-12-fluoro-2,3-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-11-ol + H2O	48% conversion, more than 99% of product (13aS)-12-fluoro-2,3-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolin-11-ol	?
reticuline + O2	-	Eschscholzia californica	(S)-scoulerine + (S)-coreximine + H2O2	50% conversion, ratio (S)-scoulerine to (S)-coreximine is >99 to <1	?

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Release 2023.1 (January 2023)