Synthesis and stereochemistry of indolactam-v, an active fragment of teleocidins. Structural requirements for tumor-promoting activity

Endo, Yasuyuki; Shudo, Koichi; Itai, Akiko; Hasegawa, Masashi; Sakai, Shin‐ichiro

doi:10.1016/s0040-4020(01)96073-9

Cited by 115 publications

(70 citation statements)

References 21 publications

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“…The 1 H and 13 C assignments of GlcNAc-TA are summarized in Table 2. The 1 H and 13 C NMR spectra of GlcNAc-TA showed a mixture of conformers in the ratio of 2 to 1 (conformer-1 : conformer-2) as observed in other teleocidins [4] and the existence of N-acetylglucosamine. The long-range coupling from an anomeric proton (H-1Ј) to a methylene carbon bearing oxygen (C-14) in the HMBC spectrum indicated the connectivity between Nacetylglucosamine and teleocidin A.…”

Section: Physico-chemical Properties and Structural Elucidationsupporting

confidence: 53%

A New Teleocidin Analog from Streptomyces sp. MM216-87F4 Induces Substance P Release from Rat Dorsal Root Ganglion Neurons

et al. 2006

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A new teleocidin analog was isolated from the fermentation medium of Streptomyces sp. MM216-87F4 and its structure was elucidated as 14-O-(Nacetylglucosaminyl) teleocidin A (GlcNAc-TA). GlcNAc-TA induces the translocation of protein kinases Ca and q fused with enhanced green fluorescent protein (PKCa -EGFP and PKCq -EGFP) to the plasma membrane in stable transfectants, and reduces intracellular calcium mobilization induced by agonists of G-protein coupled receptors in various cell lines without causing irritation of the mouse ear. Further, GlcNAc-TA sensitizes the release of excitatory neuropeptides substance P induced by capsaicin from primary-cultured dorsal root ganglion (DRG) neurons of the rat and GlcNAc-TA alone also triggers substance P release in a dose-dependent manner. This study provides the first observation that a teleocidin analog without a free hydroxyl group at C-14 acts as a PKC activator and directly induces the release of excitatory neuropeptide.

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Section: Physico-chemical Properties and Structural Elucidationsupporting

confidence: 53%

A New Teleocidin Analog from Streptomyces sp. MM216-87F4 Induces Substance P Release from Rat Dorsal Root Ganglion Neurons

et al. 2006

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“…In scheme 6, the reaction of 62 and 63 is probably difficult and a protection of an alcohol group is necessary. As compared with the reported synthetic routes (Scheme 7), the selective search route resembles the reported route [50] in several points, such as the usage of the chiral coreactant 66, the alkylation onto the 3-position of the indole ring, and the lactamization in the late step.…”

Section: -4 Synthesis Design Of Indolactam Vmentioning

confidence: 92%

“…In the reported synthetic routes from 56, 57, or 58, an optical resolution was necessary. When 56 and 57 were used as starting materials, the lactam ring was reportedly closed at almost the last step [50]. One the other hand, 58 was reacted with dichlorocarboxyl chloride to cyclize photochemically, followed by Schmidt rearrangement and N-methylation to give 34 ( Fig.…”

Section: -4 Synthesis Design Of Indolactam Vmentioning

confidence: 99%

Selective Search Focusing on Retro-Synthetically Important Bonds in A Synthesis Design System

Tanaka¹,

Kawai²,

Takabatake³

et al. 2009

J. Comput. Aided Chem.

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A new capability has been added to the synthesis design system SYNSUP [1]. The new module generates synthetic routes that focus on key-bonds. Key-bonds are selected according to their spatial relationships to chiral atoms and central atoms of functional groups. When the key-bonds cannot be formed by any reaction known to SYNSUP, then structure changes in the vicinity of the bonds are effected so that the key-bonds can be disconnected in a retro-synthetic pathway. We called the fashion "selective search". Such structure changes were studied, using 27 reported total synthesis of 25 naturally occurring compounds. This kind of selective search has been shown to be useful and practical for relatively complicated molecules.

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“…Indolactam-V (3) crystals suitable for X-ray diffraction have not been produced. The NMR studies, however, have revealed that all the teleocidins, olivoretins and indolactam-V exist in an equilibrium of the twist and sofa forms in solution (Cardellina, Marner & Moore, 1979;Endo, Shudo, Itai, Hasegawa & Sakai, 1986). It was proved that the conformational difference between teleocidins and olivoretins found in crystals was not inherent to the molecular structures but resulted from the crystalpacking forces.…”

Section: Epi-i Ndolactam-v (5)mentioning

confidence: 99%

Structures of two indolactams

Kawai¹,

Endo²,

Shudo³

et al. 1993

Acta Crystallogr Sect B

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Synthesis and stereochemistry of indolactam-v, an active fragment of teleocidins. Structural requirements for tumor-promoting activity

Cited by 115 publications

References 21 publications

A New Teleocidin Analog from Streptomyces sp. MM216-87F4 Induces Substance P Release from Rat Dorsal Root Ganglion Neurons

A New Teleocidin Analog from Streptomyces sp. MM216-87F4 Induces Substance P Release from Rat Dorsal Root Ganglion Neurons

Selective Search Focusing on Retro-Synthetically Important Bonds in A Synthesis Design System

Structures of two indolactams

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