1.14.11.11: hyoscyamine (6S)-dioxygenase

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For detailed information about hyoscyamine (6S)-dioxygenase, go to the full flat file.

Word Map on EC 1.14.11.11

1.14.11.11

scopolamine

tropane

hyoscyamus

niger

belladonna

atropa

anisodus

anticholinergic

hairy

acutangulus

anisodamine

epoxidation

2-oxoglutarate-dependent

aerial

6beta-hydroxylase

solanaceous

tanguticus

agrobacterium-mediated

metel

putrescine

datura

n-methyltransferase

tabacum

chemotype

high-value

catharanthus

pericycle

roseus

tropinone

genetically-engineered

biofunctional

gst-tag

vindoline

underground

bolt

2.1.1.53

drug development

pharmacology

Reaction

L-hyoscyamine

+

2-oxoglutarate

+

O2

=

(6S)-hydroxyhyoscyamine

+

succinate

+

CO2

Synonyms

6H6, AaH6H, AtH6H, Dih6h, H6H, HnH6H, hyoscyamine 6-hydroxylase, hyoscyamine 6beta-hydroxylase, hyoscyamine-6beta-hydroxylase, oxygenase, hyoscyamine 6beta-di-

ECTree

1 Oxidoreductases

1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

1.14.11 With 2-oxoglutarate as one donor, and incorporation of one atom of oxygen into each donor

1.14.11.11 hyoscyamine (6S)-dioxygenase

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Results	in table
39	Activating Compound
26	AA Sequence
4	Application
1	CAS Registry Number
23	Cloned(Commentary)
1	Crystallization (Commentary)
1	Expression
14	General Information
47	Inhibitors
2	kcat/KM [mM/s]
2	Ki Value [mM]
13	KM Value [mM]
14	Metals/Ions
12	Molecular Weight [Da]
20	Natural Substrates/ Products (Substrates)
8	Organic Solvent Stability
40	Organism
5	Pathway
5	pH Optimum
2	pH Range
3	pI Value
14	Protein Variants
9	Purification (Commentary)
2	Reaction
7	Reaction Type
40	Reference
41	Source Tissue
1	Specific Activity [micromol/min/mg]
3	Storage Stability
70	Substrates and Products (Substrate)
8	Subunits
45	Synonyms
1	Systematic Name
4	Temperature Optimum [°C]
2	Turnover Number [1/s]

Engineering

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Engineering on EC 1.14.11.11 - hyoscyamine (6S)-dioxygenase

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K97A

Anisodus acutangulus

the shows a 3.3fold improved hydroxylation activity compared with the wild-type enzyme

K97E

Anisodus acutangulus

the shows a 2.7fold improved hydroxylation activity compared with the wild-type enzyme

K97G

Anisodus acutangulus

the shows a 1.7fold improved hydroxylation activity compared with the wild-type enzyme

S14H

Anisodus acutangulus

the shows a 2.4fold improved hydroxylation activity compared with the wild-type enzyme

S14P

Anisodus acutangulus

the shows a 3.7fold improved hydroxylation activity compared with the wild-type enzyme

S14P/K97A

Anisodus acutangulus

double mutant shows a 4.4fold improved hydroxylation activity compared with the wild-type enzyme, and the in vivo epoxidation activity is also improved by 2.3times. With this mutant, in a 5 l bioreactor with a working volume of 3 l, scopolamine is produced via a single-enzyme-mediated two-step transformation from hyoscyamine of 500 mg/l in 97% yield (1.068 g)

D219H

Hyoscyamus niger

-

inactive mutant enzyme

D219N

Hyoscyamus niger

-

inactive mutant enzyme

H217Q

Hyoscyamus niger

-

inactive mutant enzyme

H66Q

Hyoscyamus niger

-

mutant enzyme has 97% of the activity of the wild-type enzyme

S274Q

Hyoscyamus niger

-

inactive mutant enzyme

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Release 2023.1 (January 2023)