90741-53-0Relevant academic research and scientific papers
Synthetic Haptens and Monoclonal Antibodies to the Cyanotoxin Anatoxin-a
Qui?ones-Reyes, Guillermo,Agulló, Consuelo,Mercader, Josep V.,Abad-Somovilla, Antonio,Abad-Fuentes, Antonio
, p. 9134 - 9139 (2019/07/16)
Early warning systems for monitoring toxic events may benefit from the availability of monoclonal antibodies enabling the sensitive and specific detection of anatoxin-a, a cyanotoxin involved in numerous cases of animal poisoning resulting from toxic alga
A unified approach to the synthesis of both enantiomers of anatoxin-a and homoanatoxin-a cyanotoxins
Addante-Moya, Luis G.,Agulló, Consuelo,Qui?ones-Reyes, Guillermo,Mercader, Josep V.,Abad-Fuentes, Antonio,Abad-Somovilla, Antonio
, p. 5022 - 5031 (2018/05/04)
Anatoxin-a and homoanatoxin-a are highly neurotoxic compounds produced by cyanobacteria, principally during surface water-blooms (SWBs). Owing to their powerful biological activity and unique structural characteristics, these natural alkaloids have been t
Synthesis of (±)-anatoxin-α and analogues
Parsons, Philip J.,Camp, Nicholas P.,Edwards, Neil,Ravi Sumoreeah
, p. 309 - 315 (2007/10/03)
A new and highly efficient synthesis of the potent nicotinic acetylcholine receptor agonist, anatoxin-α and its analogues is described, which uses a β-lactam ring opening-transannular cyclisation sequence to set up the bridged bicyclic framework of the natural product. The synthesis involves a cycloaddition of chlorosulfonyl isocyanate with cyclooctadiene followed by Boc protection of the resulting β-lactam. Reaction of the β- lactam with a variety of nucleophiles, followed by selenium-mediated cyclisation and oxidation gave the skeleton of anatoxin-α bearing various sidechains. The approach offers a flexible entry to useful quantities of anatoxin-α and its analogues.
Tandem reactions of anions: A short and efficient route to ±anatoxin-a
Parsons, Philip J.,Camp, Nicholas P.,Underwood, J. Mark,Harvey, Darren M.
, p. 11637 - 11642 (2007/10/03)
A new route to anatoxin-a (1) is reported which involves an anionically induced small ring opening/ring closure/ring opening cascade. The azabicyclo [4.2.1]nonane ring system of anatoxin-α is hence formed in one synthetic operation.
Synthetic and Stereochemical Studies Directed Towards Anatoxin-a
Huby, Nicholas J. S.,Kinsman, Richard G.,Lathbury, David,Vernon, Peter G.,Gallagher, Timothy
, p. 145 - 155 (2007/10/02)
The synthesis and stereocontrolled Ag1-catalysed cyclisation of a series of allenic amino esters 8a-e is described.For compounds 8a-d the cis-2,5-disubstituted pyrrolidine 9 is formed exclusively but the primary amine 8e undergoes cyclisation n
Chirospecific Synthesis of Nitrogen and Side Chain Modified Analogues of (+)-Anatoxin
Sardina, F. Javier,Howard, Michael H.,Koskinen, Ari M. P.,Rapoport, Henry
, p. 4654 - 4660 (2007/10/02)
Improvements in the chirospecific synthesis of (+)-anatoxin from D-glutamic acid have resulted in a process that gives enantiomerically pure material in reproducible 25percent overall yield.The major synthetic modifications have been in the decarbonylative iminium ion cyclization and in the introduction of the enone moiety.With multigram quantities of (+)-anatoxin thus available, a series of nitrogen and side chain modified analogues have been prepared.These analogues were chosen to provide probes for the agonist-receptor interaction model of acetylcholine.They include secondary, tertiary, and quaternary nitrogen derivatives and those in which the carbonyl function has been converted to secondary and tertiary alcohol and ester functions.
Synthetic and conformational studies on anatoxin-a: A potent acetylcholine agonist
Koskinen,Rapoport
, p. 1301 - 1309 (2007/10/02)
Anatoxin-a is a powerful nicotinic acetylcholine receptor agonist. Its recently reported synthesis has been further optimized to provide anatoxin-a of >99% optical purity in 10% overall yield. The geometry of solid anatoxin-a has been determined by X-ray
The use of nitrones in the synthesis of anatoxin-a, very fast death factor
Tufariello,Meckler,Pushpananda,Senaratne
, p. 3447 - 3453 (2007/10/02)
The synthesis of anatoxin-a (1) was completed by using the cycloaddition of 1-pyrroline-1-oxide (2) onto dienol (6), a reaction which proceeded with high stereoselectivity, regioselectivity, and site selectivity. The resultant adduct (i.e. 7) was oxidized to a second nitrone (i.e. 8) which undergoes a second closure to afford cycloadduct 9a with regiospecificity. The conversion of 9a into anatoxin-a hydrochloride (1 · HCl) was both direct and efficient.
