Ketomethylenebestatin: Synthesis and Aminopeptidase Inhibition

@article{Herranz1993KetomethylenebestatinSA,
  title={Ketomethylenebestatin: Synthesis and Aminopeptidase Inhibition},
  author={Rosario Herranz and Julia Castro‐Pichel and Ma Teresa Garc{\'i}a-L{\'o}pez and Isabel M. Gomez-Monterrey and Concepci{\'o}n P{\'e}rez and Soledad Vinuesa},
  journal={Archiv der Pharmazie},
  year={1993},
  volume={326}
}
The synthesis of (6R,5S,2RS)‐6‐amino‐5‐hydroxy‐2‐isobutyl‐4‐oxo‐7‐phenylheptanoic acid (9), a carbaanalogue of the aminopeptidase (AP) inhibitor bestatin (1) is described. This synthesis was carried out by a malonic ester alkylation with the suitably protected halomethyl ketone of (2S,3R)‐AHPBA. 
3 Citations
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References

SHOWING 1-10 OF 20 REFERENCES
An improved one-pot method for the stereoselective synthesis of the (2S,3R)-3-amino-2-hydroxy acids: key intermediates for bestatin and amastatin
La synthese d'acides [β-amino α-hydroxy] benzenebutyrique et [amino-3 hydroxy-2 methyl-5] caproique a partir des α-aminoaldehydes correspondants est etudiee
Synthesis and biological activity of a ketomethylene analogue of a tripeptide inhibitor of angiotensin converting enzyme.
An analogue of a tripeptide inhibitor of angiotensin converting enzyme, Bz-Phe-Gly-Pro, has been synthesized in which the amide bond connecting phenylalanine and glycine has been replaced by a
Arphamenines A and B, new inhibitors of aminopeptidase B, produced by bacteria.
Description de la production des arphamenines par la bacterie Chromobacterium violaceum, description de l'isolement, de la purification et de la caracterisation de ces inhibiteurs specifiques de
Bestatin, an inhibitor of aminopeptidase B, produced by actinomycetes.
papain, chymotrypsin, elastase, acid protease and thermolysin have been found in culture filtrates of actinomycetes. Recently we found that exopeptidases have a strong effect on mammalian cell
Inhibition of arginine aminopeptidase by bestatin and arphamenine analogues. Evidence for a new mode of binding to aminopeptidases.
TLDR
Analysis of the synthesis and inhibition kinetics of a new, potent inhibitor of arginine aminopeptidase and structure-activity data for a series of ketomethylene dipeptide isosteres show that the S1 and S1' subsites preferentially bind basic and aromatic side chains, respectively.
Biological activity of the main metabolites of ubenimex in humans.
TLDR
OH-Ubenimex was almost identical in inhibitory activity against mouse peritoneal resident macrophage aminopeptidases (APases) and the growth of IMC carcinoma in mice to ubenimx.
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