Additions to the azomethine group

Harada, Karou

doi:10.1002/9780470771204.ch6

Cited by 11 publications

(6 citation statements)

References 116 publications

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“…Levuglandins also can form intermolecular crosslinks. Importantly, the initial lysyllevuglandin adducts themselves are also highly reactive; the Schiff base adduct with lysine can undergo nucleophilic attack (15) and the oxidation of the pyrrole adducts generates sites of electrophilic reactivity (1,2). Thus, lysyl-LG adducts can form covalent bonds with other nucleophiles leading to intermolecular crosslinking.…”

Section: Levuglandins and Amyloid βmentioning

confidence: 99%

Cyclooxygenase-Dependent Lipid-Modification of Brain Proteins

Boutaud¹,

Andreasson²,

Zagol-Ikapitte³

et al. 2006

Brain Pathology

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Substantial evidence indicates that both beta-amyloid and cyclooxygenase activity contribute to the pathogenesis of Alzheimer disease. The immediate product of the cyclooxygenases, prostaglandin H2, rapidly rearranges in aqueous solution, with approximately 20% being converted to levuglandins E2 and D2. These gamma-ketoaldehydes are highly reactive and rapidly adduct to accessible amine groups on macromolecules, particularly the epsilon-amine of lysine residues on proteins. The immediate LG-lysine adducts are themselves reactive, and can covalently crosslink proteins. PGH2, acting via LGs, accelerates the formation of the type of oligomers of amyloid beta that has been associated with neurotoxicity. In this review, we discuss the cyclooxygenase-dependent lipid-modification of proteins by levuglandins in vitro, in cells in culture and in vivo in transgenic mice over-expressing COX in the brain.

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Section: Levuglandins and Amyloid βmentioning

confidence: 99%

Cyclooxygenase-Dependent Lipid-Modification of Brain Proteins

Boutaud¹,

Andreasson²,

Zagol-Ikapitte³

et al. 2006

Brain Pathology

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“…Hydantoins 46a and 47a were hydrolyzed with sulfuric acid to give amino acids 48a and 49a in excellent yields, respectively [50]. Treatment of 45a with KCN and NH 4 Cl in the presence of CS 2 provided a 3-exospirodithiohydantoin [51]. 3-endo-Amino acid 48a and 3-exo-aminonitrile 45a were used as starting materials for the synthesis of various 3-endo-and 3-exo-spiroheterocycles [47-49, 50, 52, 53].…”

Section: ____________________________________________________________mentioning

confidence: 99%

Complementary Ways to Diastereomers of Bridged Aminopiperidine Derivatives - A Stereochemical Challenge

Vilsmaier¹

2000

J. prakt. Chem.

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Abstract. Routes to diastereomers of constrained 4-aminopiperidines -a common pharmaceutically used diaminic building block -are realized mainly on the basis of CN-double bond species or their radicalic or anionic analogues. Kinetically controlled reactions on the one hand and thermodynamic control of reactions, reversible introduction of a repulsive group, direction of a reactant by intramolecular complexation, or involvement of radicalic or anionic intermediates with strong isomerization tendency on the other hand are the tools for a complementary accessibility of both diastereomers.

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“…Due to their aldiminic C]N-double bond, these reactive species 1 were suited for addition reactions. 2 Thus, we concentrated on different addition reactions as preferred synthetic procedures leading to the aspired target structures 2-4 ( Fig. 2).…”

Section: Introductionmentioning

confidence: 99%