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Ligand 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole

Basic Ligand Information

Molecular Structure

Related pathways

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

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Show Natural Substrate (4 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

5.5.1.31

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = hapalindole H

745842

-

5.5.1.32

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = 12-epi-hapalindole U

745842

-

5.5.1.33

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = 12-epi-fischerindole U

745842

-

5.5.1.36

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = hapalindole U

776406, 744035

-

Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Substrate (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

5.5.1.31

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = hapalindole H

745842

-

5.5.1.32

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = 12-epi-hapalindole U

745842, 745161, 745848

-

5.5.1.32

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = hapalindole U

744035

-

5.5.1.32

2 entries

5.5.1.33

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = 12-epi-fischerindole U

745842

-

5.5.1.36

3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole = hapalindole U

776406, 744035

-

Enzyme Kinetic Parameters

References & Links

Literature References (6)

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Show Reference (6 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

744035

28626997

Discovery of a calcium-dependent enzymatic cascade for the selective assembly of hapalindole-type alkaloids on the biosynthetic origin of hapalindole U

2017

Zhu, Q.; Liu, X.

Angew. Chem. Int. Ed. Engl.

56

9062-9066

745161

26629885

Hapalindole/ambiguine biogenesis is mediated by a cope rearrangement, C-C bond-forming cascade

2015

Li, S.; Lowell, A.N.; Yu, F.; Raveh, A.; Newmister, S.A.; Bair, N.; Schaub, J.M.; Williams, R.M.; Sherman, D.H.

J. Am. Chem. Soc.

137

15366-15369

745161

26629885

Hapalindole/ambiguine biogenesis is mediated by a cope rearrangement, C-C bond-forming cascade

2015

Li, S.; Lowell, A.N.; Yu, F.; Raveh, A.; Newmister, S.A.; Bair, N.; Schaub, J.M.; Williams, R.M.; Sherman, D.H.

J. Am. Chem. Soc.

137

15366-15369

745161

2 entries

745842

28288107

Decoding cyclase-dependent assembly of hapalindole and fischerindole alkaloids

2017

Li, S.; Lowell, A.; Newmister, S.; Yu, F.; Williams, R.; Sherman, D.

Nat. Chem. Biol.

13

467-469

745848

29531360

Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis

2018

Newmister, S.A.; Li, S.; Garcia-Borras, M.; Sanders, J.N.; Yang, S.; Lowell, A.N.; Yu, F.; Smith, J.L.; Williams, R.M.; Houk, K.N.; Sherman, D.H.

Nat. Chem. Biol.

14

345-351

776406

32052896

Control of stereoselectivity in diverse hapalindole metabolites is mediated by cofactor-induced combinatorial pairing of stig cyclases

2020

Li, S.; Newmister, S.; Lowell, A.; Zi, J.; Chappell, C.; Yu, F.; Hohlman, R.; Orjala, J.; Williams, R.; Sherman, D.

Angew. Chem. Int. Ed. Engl.

59

8166-8172

Links to other databases for 3-geranyl-3-[(Z)-2-isocyanoethenyl]-1H-indole

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Show Links (1 entry)