65709-93-5

Usage

Uses

Used in Agricultural Research:
Tabtoxinine beta-lactam is utilized as a subject of study in agricultural research to understand its effects on plants and to develop strategies for mitigating the damage it causes. This research is crucial for the development of resistant crop varieties and effective control measures against the bacteria that produce this toxin.
Used in Human and Animal Health Research:
Due to its toxic effects on humans and animals, tabtoxinine beta-lactam is also used as a subject in health research. This research focuses on understanding the mechanisms of its toxicity and exploring potential treatments or antidotes to counteract its harmful effects.
Used in Environmental and Public Health Studies:
Tabtoxinine beta-lactam is employed as a case study in environmental and public health studies to assess its potential impact on ecosystems and human populations. These studies aim to raise awareness about the risks associated with this toxin and to inform policies and regulations to protect public health and the environment.

InChI:InChI=1/C7H12N2O4/c8-4(5(10)11)1-2-7(13)3-9-6(7)12/h4,13H,1-3,8H2,(H,9,12)(H,10,11)

Upstream product

• 102136-55-0 benzyl (4S*,7S*)-6-benzyloxycarbonyl-1-oxo-5-oxa-2,6-diazaspiro<3.5>nonane-7-carboxylate 
• 102115-98-0 (3S*,6S*)-6-<(amino)methyl>-2,3-bis(benzyloxycarbonyl)perhydro-1,2-oxazine-6-carboxylic acid 
• 102115-96-8 (3S*,6S*)-2-benzyloxycarbonyl-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-3,6-dicarboxylic acid 
• 102115-97-9 (3S*,6S*)-2,3-bis(benzyloxycarbonyl)-6-<<(tert-butoxycarbonyl)amino>methyl>perhydro-1,2-oxazine-6-carboxylic acid 
• 137627-23-7 (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid 
• 956007-31-1 (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-hydroxy-2-azetidinone 
• 796869-92-6 (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonylamino-3'-carboxypropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone 
• 796869-99-3 benzyl (2S,5S)-5-benzyloxycarbamoyl-2-benzyloxycarbonylamino-5-hydroxy-6-methylsulfonyloxyhexanoate 
• 796869-91-5 (3S,3'S)-1-benzyloxy-3-(3'-benzyloxycarbonyl-3'-benzyloxycarbonylaminopropyl)-3-tert-butyldimethylsilyloxy-2-azetidinone 
• 137627-18-0 (3RS,3'E,5'R)-1-(tert-butyldimethylsilyl)-3-<5'-(methylthio)hex-3'-enyl>-3-<(trimethylsilyl)oxy>-2-oxoazetidine 
• 137627-20-4 (3RS,3'S,4'E)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>hex-4'-enyl>-3-hydroxy-2-oxoazetidine 
• 137627-22-6 (3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone 
• 137627-21-5 (3S,3'S)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone 

Downstream Products

• 56599-17-8 tabtoxinine-δ-lactam 

Relevant academic research and scientific papers

Stereoselective Synthesis of Tabtoxinine-β-lactam by Using the Vinylogous Mukaiyama Aldol Reaction with Acetate-Type Vinylketene Silyl N,O-Acetal and α-Keto-β-lactam

Stereoselective total synthesis of tabtoxinine-β-lactam has been achieved. The vinylogous Mukaiyama aldol reaction with vinylketene silyl N,O-acetal and α-keto-β-lactam proceeded to afford the adduct possessing a TβL-skeleton with a tert-alcohol in high yield and stereoselectivity. Stereoselective introduction of the amino group has been accomplished by azidation at the α position of the imide followed by hydrogenolysis. A straightforward method to achieve the potent inhibitor of glutamine synthetase, possessing both α-hydroxy-β-lactam and α-amino acid moieties, has been established.

Synthesis of (-)-tabtoxinine-β-lactam, the phytotoxin of tobacco wildfire disease

Synthesis of (-)-tabtoxinine-β-lactam and its (3R)-isomer, the cause of tobacco wildfire disease, was achieved from L-serine using a zinc-mediated coupling reaction, Sharpless asymmetric dihydroxylation and lactamization of β-mesyloxy benzylhydroxamate amide as the key steps. Georg Thieme Verlag Stuttgart.

Enantiospecific Synthesis of (-)-Tabtoxinine &β-Lactam

A convergent, 10-step synthesis of optically active tabtoxinine β-lactam has been described.Key features of the synthetic route include (1) preparation of a new γ-cation amino acid synthon, (-)-4, and its use as an electrophile (3 -> 11); (2) the one-pot conversion of methyl sulfide 11 to the Cbz-protected amine 12 via stereoselective sulfilimine rearrangement; and (3) chemoselective lactone ring opening in spiro lactam 15a.Synthons (-)-4 and 3 are available on a semipreparative scale.

Synthesis of a Naturally Occuring Inhibitor of Glutamine Synthetase, Tabtoxinine-β-lactam

(+/-)-Tabtoxinine-β-lactam, a potent inhibitor of glutamine synthetase, has been synthesised by a route involving a nitroso Diels-Alder reaction.