- A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils
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Formyl-Met-Leu-Phe-OH (fMLP) binds to formyl peptide receptors, FPR1 and FPR2, and evokes migration and superoxide anion production in human neutrophils. To obtain a more effective and selective ligand, fMLP analogs in which the Phe residue was substitute
- Hayashi, Ryo,Miyazaki, Masaya,Osada, Satoshi,Kawasaki, Hiroshi,Fujita, Ichiro,Hamasaki, Yuhei,Kodama, Hiroaki
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supporting information
p. 668 - 675
(2013/02/25)
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- Catalytic asymmetric synthesis of nitrocyclopropane carboxylates
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A Cu(I)-catalyzed asymmetric cyclopropanation of alkenes with an iodonium ylide has been developed. The copper source, hypervalent iodine source, solvent, and additives all have a significant effect on the yields and enantioselectivities. High enantioselectivity (up to 99:1 er) and diastereoselectivity (95:5 dr trans/cis) were achieved for a wide range of alkenes. Conditions were developed to convert the trans products to the cis isomers. In addition, 1-nitrocyclopropyl carboxylates were transformed into the corresponding substituted cyclopropane amino acids and aminocyclopropanes. Moreover, a comparative study between Zn- and In-mediated reduction reactions of the nitro group in these compounds with regards to the er erosion in the process is also documented.
- Moreau, Benoit,Alberico, Dino,Lindsay, Vincent N.G.,Charette, Andre B.
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p. 3487 - 3496
(2012/06/04)
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- Asymmetric cyclopropanations by rhodium(II) N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes. Practical enantioselective synthesis of the four stereoisomers of 2-phenylcyclopropan-1-amino acid
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The rhodium N-(arylsulfonyl)prolinate catalyzed decomposition of vinyldiazomethanes in the presence of alkenes leads to a very general method for the synthesis of functionalized cyclopropanes in a highly diastereoselective and enantioselective mode. A det
- Davies, Huw M. L.,Bruzinski, Paul R.,Lake, Debra H.,Kong, Norman,Fall, Michael J.
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p. 6897 - 6907
(2007/10/03)
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- Preparation of dipeptoid mimetics for the tetrapeptide cholecystokinin, CCK(30-33)
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The diastereoselective synthesis of 2,3-methanophenylalanine methyl esters (5) has been achieved in 58% yield. The preparation of the dehydropeptides (1, R = Me; 2, R = H) and the cyclopropylpeptides (3, R = Me; 4, R = H) possessing good binding affinities for the CCK-A and CCK-B receptors is described. Conformational studies of the dipeptide esters 1 and 3 indicated the presence of a β-turn within the peptide backbone, although there was no preference in type. The Phe and Trp moieties, however, did prefer to be situated on the same side of the peptide turn which is favourable for receptor binding.
- Walford,Campbell,Horwell
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p. 188 - 191
(2007/10/03)
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