TryptophanC5-,C6-andC7-Prenylating Enzymes Displaying a Preference for C-6 of the Indole Ring in the Presence of Unnatural Dimethylallyl Diphosphate Analogues

2015 ◽  
Vol 357 (5) ◽  
pp. 975-986 ◽  
Author(s):  
Julia Winkelblech ◽  
Mike Liebhold ◽  
Jakub Gunera ◽  
Xiulan Xie ◽  
Peter Kolb ◽  
...  
Keyword(s):  
Indole Ring ◽  
Dimethylallyl Diphosphate

Rearrangements in the mechanisms of the indole alkaloid prenyltransferases

2013 ◽  
Vol 85 (10) ◽  
pp. 1935-1948 ◽  
Author(s):  
Niusha Mahmoodi ◽  
Qi Qian ◽  
Louis Y. P. Luk ◽  
Martin E. Tanner
Keyword(s):  
Indole Alkaloid ◽  
Ion Pair ◽  
Pair Formation ◽  
Tryptophan Residue ◽  
Cope Rearrangement ◽  
Indole Ring ◽  
Structural Homology ◽  
Dimethylallyl Diphosphate ◽  
Free Tryptophan ◽  
Dimethylallyltryptophan Synthase

The indole prenyltransferases are a family of metal-independent enzymes that catalyze the transfer of a prenyl group from dimethylallyl diphosphate (DMAPP) onto the indole ring of a tryptophan residue. These enzymes are remarkable in their ability to direct the prenyl group in either a “normal” or “reverse” fashion to positions with markedly different nucleophilicity. The enzyme 4-dimethylallyltryptophan synthase (4-DMATS) prenylates the non-nucleophilic C-4 position of the indole ring in free tryptophan. Evidence is presented in support of a mechanism that involves initial ion pair formation followed by a reverse prenylation at the nucleophilic C-3 position. A Cope rearrangement then generates the C-4 normal prenylated intermediate and deprotonation rearomatizes the indole ring. The enzyme tryprostatin B synthase (FtmPT1) catalyzes the normal C-2 prenylation of the indole ring in brevianamide F (cyclo-L-Trp-L-Pro). It shares high structural homology with 4-DMATS, and evidence is presented in favor of an initial C-3 prenylation (either normal or reverse) followed by carbocation rearrangements to give product. The concept of a common intermediate that partitions to different products via rearrangements can help to explain how these evolutionarily related enzymes can prenylate different positions on the indole ring.

Enantioselective α-Aminophosphonate Functionalization of Indole Ring through an Organocatalyzed Friedel–Crafts Reaction

2018 ◽  
Vol 84 (2) ◽  
pp. 1094-1102 ◽  
Author(s):  
Aitor Maestro ◽  
Edorta Martinez de Marigorta ◽  
Francisco Palacios ◽  
Javier Vicario
Keyword(s):  
Indole Ring

Propargylamines in Pd/Cu-catalyzed tandem coupling-cyclization-N-deprotection in a single pot: Construction of N-unsubstituted vs N-sulfonyl indole ring

2021 ◽  
pp. 153213
Author(s):  
Gangireddy Sujeevan Reddy ◽  
Jetta Sandeep Kumar ◽  
B. Thirupataiah ◽  
Kazi Amirul Hossain ◽  
Suresh Babu Nallapati ◽  
...  
Keyword(s):  
Indole Ring

Atom‐economical Approaches to 1,5‐Benzodiazepines Containing Indole Ring via Fe 3 O 4 @SiO 2 ‐PTSA‐catalyzed Multi‐component Domino Reactions

2020 ◽  
Vol 5 (44) ◽  
pp. 14056-14061
Author(s):  
KaiYue Zhang ◽  
Jing Li ◽  
KaiXuan Wang ◽  
Xiaoying An ◽  
LanZhi Wang
Keyword(s):  
Indole Ring ◽  
Domino Reactions

scholarly journals Arylamine N-methyltransferase. Methylation of the indole ring.

1982 ◽  
Vol 257 (13) ◽  
pp. 7531-7535
Author(s):  
E S Lyon ◽  
W B Jakoby
Keyword(s):  
Indole Ring

ChemInform Abstract: Divergent Reactions of Indoles with Aminobenzaldehydes: Indole Ring-Opening vs. Annulation and Facile Synthesis of Neocryptolepine.

ChemInform ◽  
2012 ◽  
Vol 43 (9) ◽  
pp. no-no
Author(s):  
Matthew K. Vecchione ◽  
Aaron X. Sun ◽  
Daniel Seidel ◽  
et al. et al.
Keyword(s):  
Ring Opening ◽  
Indole Ring ◽  
Facile Synthesis

scholarly journals Diethyl 3,3′-[(3-fluorophenyl)methylene]bis(1H-indole-2-carboxylate)

IUCrData ◽  
2020 ◽  
Vol 5 (7) ◽  
Author(s):  
Hong Jiang ◽  
Yu-Long Li ◽  
Jin Zhou ◽  
Hong-Shun Sun ◽  
Qing-Yu Zhang ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Indole Ring ◽  
Ring Systems ◽  
Compound C ◽  
The Mean ◽  
Supramolecular Chains

In the title compound, C29H25FN2O4, the mean planes of the indole ring systems are approximately perpendicular to one another [dihedral angle = 88.3 (4)°]. The benzene ring is twisted with respect to the indole ring systems by 49.8 (5) and 77.6 (3)°. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into the inversion dimers which are further linked into supramolecular chains propagating along the [110] direction.

scholarly journals (Z)-3-(1-Chloroprop-1-enyl)-2-methyl-1-phenylsulfonyl-1H-indole

2013 ◽  
Vol 69 (12) ◽  
pp. o1781-o1781 ◽  
Author(s):  
M. Umadevi ◽  
V. Saravanan ◽  
R. Yamuna ◽  
A. K. Mohanakrishnan ◽  
G. Chakkaravarthi
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Phenyl Ring ◽  
Three Dimensional ◽  
Ring System ◽  
Indole Ring ◽  
Compound C ◽  
Dimensional Network ◽  
A Chain

In the title compound, C18H16ClNO2S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The molecular structure is stabilized by a weak intramolecular C—H...O hydrogen bond. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming a chain along [10-1]. C—H...π interactions are also observed, leading to a three-dimensional network.

scholarly journals Crystal structures of three indole derivatives: 3-ethnyl-2-methyl-1-phenylsulfonyl-1H-indole, 4-phenylsulfonyl-3H,4H-cyclopenta[b]indol-1(2H)-one and 1-{2-[(E)-2-(5-chloro-2-nitrophenyl)ethenyl]-1-phenylsulfonyl-1H-indol-3-yl}ethan-1-one chloroform monosolvate

2015 ◽  
Vol 71 (9) ◽  
pp. 1036-1041
Author(s):  
S. Gopinath ◽  
K. Sethusankar ◽  
Bose Muthu Ramalingam ◽  
Arasambattu K. Mohanakrishnan
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angles ◽  
Indole Derivatives ◽  
Indole Ring ◽  
Asymmetric Unit ◽  
Ring Systems ◽  
Benzene Rings ◽  
Independent Molecules

The title compounds, C17H13NO2S, (I), C17H13NO3S, (II), and C24H17ClN2O5S·CHCl3, (III), are indole derivatives. Compounds (I) and (II) crystalize with two independent molecules in the asymmetric unit. The indole ring systems in all three structures deviate only slightly from planarity, with dihedral angles between the planes of the pyrrole and benzene rings spanning the tight range 0.20 (9)–1.65 (9)°. These indole ring systems, in turn, are almost orthogonal to the phenylsulfonyl rings [range of dihedral angles between mean planes = 77.21 (8)–89.26 (8)°]. In the three compounds, the molecular structure is stabilized by intramolecular C—H...O hydrogen bonds, generatingS(6) ring motifs with the sulfone O atom. In compounds (I) and (II), the two independent molecules are linked by C—H...O hydrogen bonds and C—H...π interactions, while in compound (III), the molecules are linked by C—H...O hydrogen bonds, generatingR22(22) inversion dimers.

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