- Synthesis of phosphinic acid analogues of glycyl-glycine and crystal structure of n-glycyl-aminomethyl-(phenylphosphinic) acid
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Phosphinic acid analogues of Gly-Gly, NH2CH2CONHCH2-P(R)O2H (R=Me, Ph, t-Bu), were synthesised by the active ester method from free aminomethylphosphinic acids purified on cation exchange resins. The crystal and
- Lukas, Michal,Vojtisek, Pavel,Hermann, Petr,Rohovec, Jan,Lukes, Ivan
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- A convenient one-pot preparation of disubstituted phosphinic acids derived from simple amino acids and proline
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A facile method for the preparation of both 2-pyrrolidinyl-substituted phosphinic acids and 1-aminoalkylphosphinic acids is described. Reaction of 1-pyrroline trimer or N-tritylalkanamine with bis(trimethylsilyl)phosphonite, followed by silylation with N,O-bis(trimethylsilyl)acetamide gives an intermediate which is used in a Michael addition reaction or an Arbuzov reaction.
- Borloo,Jiao,Wojtowicz,Rajan,Verbruggen,Augustyns,Haemers
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- Process for the preparation of aminomethanephosphonic acid and aminomethylphosphinic acids
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Aminomethanephosphonic acid and aminomethylphosphinic acids are interesting as biologically active compounds or as intermediates for the preparation of biologically active compounds. According to the invention, such compounds of the formula I STR1 in which R1 is OH, C1 -C4 -alkyl or phenyl, can be prepared in a technically simple manner by reacting compounds of the formula II STR2 in which R2 is H, C1 -C6 -alkyl, benzyl, phenyl, optionally substituted by C1 -C4 -alkyl, -alkoxy and/or halogen, and R1 is as defined above, with water, at 80° to 300° C.
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- Complexing properties of phosphinic analogues of glycine
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A series of aminomethylphosphinic acids H2NCH2PRO2H (R = H, Me, But or Ph) was synthesized and the acid-base and complexing properties with CoII, NiII and CuII were determined pH
- Rohovec, Jan,Lukes, Ivan,Vojtisek, Pavel,Cisarova, Ivana,Hermann, Petr
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p. 2685 - 2691
(2007/10/03)
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- Peptides containing the novel Methylphosphinamide Transition-State Isostere
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A convenient route towards the synthesis of peptides containing the methylphosphinamide moiety as a novel transition-state isostere of the amide bond hydrolysis is described.The key step being the coupling of a methylphosphinic chloride with an amino acid
- Moree, Wilna J.,Marel, Gijs A. van der,Boom, Jacques H. van,Liskamp, Rob M. J.
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p. 11055 - 11064
(2007/10/02)
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- Process for the preparation of α-aminoalkylphosphonic acids and of α-aminoalkylphosphinic acids
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α-Aminoalkylphosphonic and α-aminoalkylphosphinic acids of the formula I STR1 where n=1 or 0, R1 =H, CH3 or CH2 --C6 H5 R2 =H (for n=1) and also=alkyl or phenyl (for n=0) are prepared by Hofmann deradation from compounds of the formula II STR2 wherein n and R1 have the same meaning as in formula I, R3 =alkyl (for n=1), alkyl or phenyl (for n=0), and Mp+ =p-valent cation, with subsequent working up in the known manner. Some of the compounds I are biologically active, and some are intermediates for the preparation of biologically active compounds.
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- Synthesis, Enzyme-Substrate Interaction, and Herbicidal Activity of Phosphoryl Analogues of Glycine
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The interactions of hydrophosphoryl compounds 1-10 and 1,3,5-triacetylhexahydro-1,3,5-triazine furnish the N-acetylated (aminomethyl)phosphoryl compounds 11-20, which, upon acidic hydrolysis, lead to 3, 6, 9, and 21-24.Strict selectivity is observed in the enzyme-catalyzed hydrolysis with the enzymes α-chymotrypsin, phosphodiesterase I, and alkaline phosphatase.Some of the synthesized materials exhibit herbicidal and antitumor activity.
- Natchev, Ivan A.
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p. 861 - 868
(2007/10/02)
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