- Biocatalyzed kinetic resolution of racemic mixtures of chiral α-aminophosphonic acids
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Several fungal species namely: Aspergillus niger, Aspergillus parasiticus, Penicillium funiculosum, Trigonopsis variabilis and two different strains of Fusarium oxysporum were tested toward racemic mixtures of following phosphonic acids: 1-amino-2-methylp
- Kozyra, Kinga,Brzezinska-Rodak, Malgorzata,Klimek-Ochab, Magdalena,Zymanczyk-Duda, Ewa
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- A Highly Convenient Route to Optically Pure α-Aminophosphonic Acids
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Pure diastereomers, obtained simply and directly by reaction of hypophosphorous acid salts of (R)(+) or (S)(-) - N-α-methylbenzylamine with aldehydes, can be simultaneously deprotected and oxidised in one step to provide a highly convenient synthesis of α-aminophosphonic acids in high optical purity.
- Hamilton, Robert,Walker, Brian,Walker, Brian J.
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p. 4451 - 4454
(2007/10/02)
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- Enantioselective Synthesis of α-Amino Phosphonic Acids by an Application of Stereoselective Opening of Homochiral Dioxane Acetals with Triethyl Phosphite
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Stereoselective opening of homochiral acetals (2a-c) with triethyl phosphite was applied to the enantioselective synthesis of phosphono alcohols (1a-c), which were succssefully converted to the α-amino phosphonic acid diethyl esters (6a-c).
- Yokomatsu, Tsutomu,Shibuya, Shiroshi
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p. 377 - 378
(2007/10/02)
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- New α-amino phosphonic acid derivatives of vinblastine: Chemistry and antitumor activity
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A series of new amino phosphonic acid derivatives of vinblastine (1, VLB) has been synthesized and tested in vitro and in vivo for antitumor activity. The compounds were obtained from O4-deacetyl-VLB azide (5). All of the new products studied w
- Lavielle,Hautefaye,Schaeffer,Boutin,Cudennec,Pierre
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p. 1998 - 2003
(2007/10/02)
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- 133. Nucleophilic Additions to N-Glycosylnitrones. Part IV. Asymmetric Synthesis of N-Hydroxy-α-aminophosphonic and α-Aminophosphonic Acids
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The addition of phosphite anions and of tris(trimethylsilyl)phosphite (P(OSiMe3)3) to N-glycosyl-C-aryl-nitrones was examined.While these nitrones proved inert towards the phosphite anions, they reacted with P(OSiMe3)3 under catalysis by Lewis acids.Thus,
- Huber, Rolf,Vasella, Andrea
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p. 1461 - 1476
(2007/10/02)
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- 181. Nuchleophilic Additions to N-Glycosylnitrones Asymmetric Synthesis of α-Aminophosphonic Acids
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The hypothesis which explains the diastereoselectivity of the 1,3-dipolar cycloaddition of the N-glycosylnitrones 1-3 leading to the 5,5-disubstituted isoxazolidines 4-6 on the basis of a kinetic anomeric effect predicts that nucleophiles should add to N-
- Huber, Rolf,Knierzinger, Andreas,Obrecht, Jean-Pierre,Vasella, Andrea
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p. 1730 - 1747
(2007/10/02)
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- 1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids
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The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.
- Baylis, E. Keith,Campbell, Colin D.,Dingwall, John G.
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p. 2845 - 2853
(2007/10/02)
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- Optically active 1-aminoalkanephosphonic acids. Dibenzoyl-L-tartaric anhydride as an effective agent for the resolution of racemic diphenyl 1-aminoalkanephosphonates
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Optically active phosphonic analogues of alanine, valine, leucine, phenylalanine, and phenylglycine were obtained by resolution of diphenyl 1-aminoalkenephosphonates with dibenzoyl-L-tartaric acid anhydride.
- Kafarski, Pawel,Lejczak, Barbara,Szewczyk, Jerzy
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p. 2425 - 2430
(2007/10/02)
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