Studies on the Synthesis of Chemotherpeutics. Part XI. Synthesis and Antibacterial Activities of Phosphonopeptides

Kametani, Tetsuji; Kigasawa, Kazuo; Hiiragi, Mineharu; Wakisaka, Kikuo; Haga, Satoshi; Sugi, Hideo; Tanigawa, Keizo; Suzuki, Yukio; Fukawa, Kazunaga; Irino, Osamu; Saita, Osamu; Yamabe, Shigeru

doi:10.3987/r-1981-07-1205

Cited by 67 publications

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“…The N-hydroxya -aminophosphonic acids and a -aminophosphonic acids, analogs of the corresponding amino acids, exert biological activities, which have been shown to depend on the absolute configuration [8] -.…”

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confidence: 99%

Nucleophilic Additions to N‐Glycosylnitrones. Asymmetric Synthesis of α‐Aminophosphonic Acids

Huber¹,

Knierzinger²,

Obrecht³

et al. 1985

Helvetica Chimica Acta

105

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Dedicated to Professor Dr. A . Eschenmoser on the occasion of his 60th birthday (6.V1.85)The hypothesis which explains the diastereoselectivity of the 1,3-dipolar cycloaddition of the N-glycosylnitrones 1-3 leading to the 5,s-disubstituted isoxazolidines 4 6 on the basis of a kinetic anomeric effect predicts that nucleophiles should add to N-glycosylnitrones with a high degree of diastereoselectivity. To test this prediction, the nucleophilic addition of lithium and potassium dialkylphosphites to the crystalline (Z)-nitrone 11, prepared from oxime 9 and (benzy1oxy)acetaldehyde has been examined. The addition of lithium phosphites gave the N-glycosyl-N-hydroxyaminophosphonates 12-16 (d. e. 78-92%) in high yields (Scheme 4). The addition of potassium phosphites showed a much lower diastereoselectivity. Glycoside cleavage, hydrogenolysis, and dealkylation of 12-16 gave (+)-(S)-phosphoserine (+)-19 (34-45 % from 9).Its absolute configuration was confirmed by an X-ray analysis of the N-(3,3,3-trifluoro-2-methoxy-2-phenylpropionyl) derivative 24. Similarly, the crystalline nitrone 25 gave the N-glycosyl-N-hydroxyaminophosphonate 26, which was transformed into ( +)-(S)-phosphovaline (+)-31 (42% from 9). The diastereoselectivity of the nucleophilic addition and the enantiomeric purity of ( + )-31 were determined by the analysis of the derivative 30 (d.e. 92%) and 32 (d.e. 93%), respectively. The addition of lithium diethyl phosphite to the nitrone 33, prepared in situ, gave the N-glycosyl-N-hydroxyaminophosphonate 34 (41 %;d.e. 91 YO), which was transformed in (+)-(S)-phosphoalanine (+)-37 (21 Sb from 9).

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mentioning

confidence: 99%

Nucleophilic Additions to N‐Glycosylnitrones. Asymmetric Synthesis of α‐Aminophosphonic Acids

Huber¹,

Knierzinger²,

Obrecht³

et al. 1985

Helvetica Chimica Acta

105

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“…There have been many articles concerning the synthesis of phosphonopeptides with an ␣-aminophosphonic acid in the C-terminal position, including the acid chloride method [4,5], activated ester method [6,7], condensation method [8,9], mixed anhydride method [10,11], and so on. All these methods, however, required an ␣-aminophosphonic ester to be synthesized as an intermediate, which often required multistep reactions to effectuate.…”

Section: Synthesis Of Phosphonopeptidesmentioning

confidence: 99%

Synthesis of novel phosphonopeptide derivatives and their biological activity

Dai

Chen

1997

Heteroat. Chem.

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In order to search for novel herbicides with high activity and selectivity, a series of N‐p‐toluenesulfonyl phosphonopeptide derivatives has been designed and synthesized by the condensation reaction of diphenyl α‐aminoalkylphosphonates and 1‐p‐toluenesulfonamido‐acetyl chloride. Their structures were confirmed by 1H NMR spectroscopy and elemental analyses. The results of bioassay showed that some of these compounds possess potential anti‐TMV (Tobacco Mosaic Virus) activity. © 1997 John Wiley and Sons, Inc. Heteroatom Chem 8: 279–282, 1997.

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“…8-1z Biological activities of these compounds strongly depend on the absolute configuration of the C,~ atom. [13][14][15] Thus, asymmetric synthesis of this class of compounds is of particular interest.…”

Section: -)_(r)-ta_hydroxy_ Benzytphosphonic Acidmentioning

confidence: 99%

Asymmetric synthesis of α-substituted alkylphosphonates based on symmetrical dialkyl phosphites

et al. 1999

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Chiral C2-symmetrical dialkyl phosphites and C3-symmetrical trialkyl phosphites, derived from (-)-borneol. (-)-menthol, and 1,2:5,6-di-O-isopropylidene-ct-n-glucofuranose, were studied as the starting reagents for the preparation of ctural organophosphorus compounds. The reactions of C2-symmetrical dialkyl phosphites and Cusymmetrical trialkyl phosphites with aldehydes and amines or aldehydes are accompanied by asymmetrical induction at the ~z-carbon atom to yield optically active c.~-aminoalkytphosphonates or ct-hydroxyalkylphosphonates, respectively. The stereoselectivity of the reaction depends on the structure of the starling compounds and the reaction conditions.

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Studies on the Synthesis of Chemotherpeutics. Part XI. Synthesis and Antibacterial Activities of Phosphonopeptides

Cited by 67 publications

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Nucleophilic Additions to N‐Glycosylnitrones. Asymmetric Synthesis of α‐Aminophosphonic Acids

Nucleophilic Additions to N‐Glycosylnitrones. Asymmetric Synthesis of α‐Aminophosphonic Acids

Synthesis of novel phosphonopeptide derivatives and their biological activity

Asymmetric synthesis of α-substituted alkylphosphonates based on symmetrical dialkyl phosphites

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