107072-65-1Relevant articles and documents
Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX
Jia, Chao,Yang, Ke-Wu,Liu, Cheng-Cheng,Feng, Lei,Xiao, Jian-Min,Zhou, Li-Sheng,Zhang, Yi-Lin
, p. 482 - 484 (2012/03/11)
VanX, a Zn(II)-dependent D-ala-D-ala dipeptidase, is essential for vancomycin resistance in Enterococcus faecium. The enzymatic activity of VanX was previously found to be inhibited competitively by 2-{[(1-aminoethyl) (hydroxy) phosphoryl]oxy} propanoic acid (1B). Here we report the synthesis and characterization of seven phosphonate dipeptide analogs of D-ala-D-ala with various substituent, the activity evaluation indicated that six of these phosphonate analogs inhibit VanX with IC50 of 0.48-8.21 mM. These data revealed a structure-activity relationship which is that the large substituent group on β-carbon resulted in low binding affinity of the phonphonate analog to VanX. This information will be helpful to guide the design and synthesis of the tightly-binding inhibitors for VanX.
Phosphonamidate and phosphothioate dipeptides as potential inhibitors of VanX
Yang, Ke-Wu,Brandt, Jeffrey J.,Chatwood, Lisa L.,Crowder, Michael W.
, p. 1085 - 1087 (2007/10/03)
In an effort to prepare novel inhibitors of VanX, N-[(1-aminoethyl)hydroxyphosphinyl]-D-alanine 1 and S-[(aminoethyl)hydroxyphosphinyl]-thiolacetic acid 2 were synthesized and evaluated as inhibitors of VanX. Phosphonamidate 1 was shown to be a partial co
TOWARD NEW INHIBITORS OF D-ALANINE:D-ALANINE LIGASE: THE SYNTHESIS OF 3-AMINO BUTENYLPHOSPHONIC AND AMINOPHOSPHONAMIDIC ACIDS.
Vo-Quang, Y.,Gravey, A. M.,Simonneau, R.,Vo-Quang, L.,Lacoste, A. M.,le Goffic, F.
, p. 6167 - 6170 (2007/10/02)
The condensation of sodium salt of tetraethyl methylenediphosphonate with N-Cbz alaninal followed by the standard acidolytic removal of protecting groups provides an efficient method for the synthesis of 3-aminobutenylphosphonic acid E 3 ; N-Cbz-aminophos
