58455-89-3Relevant academic research and scientific papers
Inhibition of tRNA-dependent ligase MurM from Streptococcus pneumoniae by phosphonate and sulfonamide inhibitors
Cressina, Elena,Lloyd, Adrian J.,De Pascale, Gianfranco,James Mok,Caddick, Stephen,Roper, David I.,Dowson, Christopher G.,Bugg, Timothy D.H.
experimental part, p. 3443 - 3455 (2009/10/10)
Ligase MurM catalyses the addition of Ala from alanyl-tRNAAla, or Ser from seryl-tRNASer, to lipid intermediate II in peptidoglycan biosynthesis in Streptococcus pneumoniae, and is a determinant of high-level penicillin resistance. Phosphorus-based transition state analogues were designed as inhibitors of the MurM-catalysed reaction. Phosphonamide analogues mimicking the attack of a lysine nucleophile upon Ala-tRNAAla showed no inhibition of MurM, but adenosine 3′-phosphonate analogues showed inhibition of MurM, the most active being a 2′-deoxyadenosine analogue (IC50 100 μM). Structure/function studies upon this analogue established that modification of the amino group of the aminoalkylphosphonate resulted in loss of potency, and modification of the adenosine 5′-hydroxyl group with either a t-butyl dimethyl silyl or a carbamate functional group resulted in loss of activity. A library of 48 aryl sulfonamides was also screened against MurM using a radiochemical assay, and two compounds showed sub-millimolar inhibition. These compounds are the first small molecule inhibitors of the Fem ligase family of peptidyltransferases found in Gram-positive bacteria.
A convenient method for the synthesis of N-protected 1-aminoalkylphosphonate mixed monothioesters and dithioesters
Xu,Wei
, p. 1489 - 1497 (2007/10/03)
A series of N-protected 1-aminoalkylphosphonate mixed monothioesters and dithioesters were synthesized using one-pot reactions of benzyl carbamate, aldehydes and alkoxyphosphine dichlorides or alkylthiophosphine dichloride, followed by alcoholysis with thiol or alcohols in the presence of triethylamine.
A novel and convenient method for synthesizing unsymmetrical - Benzyloxycarbonyl-protected 1-amino-1-arylalkylphosphonate mixed diesters
Xu,Fu
, p. 1223 - 1226 (2007/10/03)
Unsymmetrical N-benzyloxycarbonyl-protected 1-amino-1-arylalkylphosphonate mixed diesters were synthesized using a one-pot reaction involving benzyl carbamate, aromatic aldehydes and alkoxydichlorophosphine, followed by treatment with alcohols in the presence of triethylamine. The reactions were followed by 31P NMR and a mechanism is proposed.
A facile synthesis of N-protected 1-aminoalkylphosphonamidate derivatives
Xu,Fu
, p. 4137 - 4145 (2007/10/03)
N-protected 1-amino-alkylphosphonamidates were synthesized using one-pot reactions of benzyl carbamate, aldehydes and alkoxyphosphine dichlorides and then with amines in the presence of triethylamine.
A modified method for synthesis of alkyl hydrogen α-(benzyloxycarbonylamino)-benzylphosphonates
Dai, Qing,Chen, Ruyu
, p. 3341 - 3347 (2007/10/03)
A series of alkyl hydrogen α-(benzyloxycarbonylamino)benzylphosphosphonates are prepared from benzyl carbamate, substituted benzaldehydes and alkoxydichlorophosphine in acetyl chloride and subsequent hydrolysis. Compared with the previous methods, the reaction avoids producing the corresponding diesters and thus improves the yields of the products.
Studies on Organophosphorus Compounds; XLI. A Convenient Synthesis of Alkyl Hydrogen α-(Benzyloxycarbonylamino)benzylphosphonates
Yuan, Chengye,Wang, Guohong
, p. 256 - 258 (2007/10/02)
Alkyl hydrogen α-(benzyloxycarbonylamino)benzylphosphonates are prepared from substituted benzaldehydes, benzyl carbamate, and phosphorus(III) chloride in acetic acid containing thionyl chloride and subsequent alcoholysis.The reactions proceed smoothly at
A Convenient Synthesis of Alkyl Hydrogen 1-(Benzyloxycarbonylamino)-alkanephosphonates
Hoffmann, Maria
, p. 557 - 559 (2007/10/02)
Alkyl hydrogen 1-(benzyloxycarbonylamino)-alkanephosphonates are prepared by condensation of 1-(benzyloxycarbonylamino)-alkanephosphonic acids with primary and secondary alcohols in the presence of thionyl chloride in dimethylformamide.
AMINOPHOSPHONIC ACIDS. PART XVII. SYNTHESES AND PROPERTIES OF N-ACYL-1-AMINOALKANEPHOSPHONIC ACID 2-CYANOETHYL ESTERS
Szewczyk, Jerzy,Rachon, Janusz,Wasielewski, Czeslaw
, p. 477 - 483 (2007/10/02)
2-cyanoethyl monoesters and non-symmetrical 2-cyanoethyl-methyl diesters of N-acyl-1-amino-alkanephosphonic acid were prepared.Properties of 2-cyanoethyl esters as protecting groups of a phosphonic group were examined.
AMINOPHOSPHONIC ACIDS. PART XV. 2,2,2-TRICHLOROETHYL AS A PROTECTIVE OF PHOSPHONIC GROUP IN N-ACYL-1-AMINOALKANEPHOSPHONIC ACIDS
Szewczyk, Jerzy,Wasielewski, Czeslaw
, p. 1985 - 1994 (2007/10/02)
Methods of synthesizing N-acyl-1-aminoalkanephosphonic acid 2,2,2-trichloroethyl monoesters and alkyl-2,2,2-trichloroethyl diester were described.Various methods of selective non-hydrolytic cleavage of phosphonic and amino groups protections were investig
