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Chemical Compound Review:

AC1NUIC2 (2R,3S,5R)-2-benzyl-3- hydroxy-5-[[(2S)-3...

Synonyms: Hydroxyethylene dipeptide isostere, Noa-His-Phe.psi.[CH2CH(OH)]Phe-Ile-Amp

Kempf, D.J. et al., Shearman, M.S. et al., Sakurai, M. et al., Tian, G. et al., Bugelski, P.J. et al., et al.

Shearman, Beher, Clarke, Lewis, Harrison, Hunt, Nadin, Smith, Stevenson, Castro, Tian, Sobotka-Briner, Zysk, Liu, Birr, Sylvester, Edwards, Scott, Greenberg,

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Disease relevance of AIDS006007

The preferred stereochemistry of the hydroxyethylene dipeptide isostere was found to be the opposite to that required for inhibition of the HIV-1 aspartyl protease, a factor which may contribute to the observed specificity of this compound [1].
An efficient, stereoselective synthesis of the hydroxyethylene dipeptide isostere core for the HIV protease inhibitor A-792611 [2].

High impact information on AIDS006007

These compounds possess a hydroxyethylene dipeptide isostere of aspartyl protease transition state analogs, suggesting gamma-secretase may be an aspartyl protease [3].
Preorganization of the hydroxyethylene dipeptide isostere: the preferred conformation in solution resembles the conformation bound to BACE [4].
The synthesis of a series of renin inhibitors in which the P2 and P3 amino acids are replaced with the hydroxyethylene dipeptide isostere is reported [5].
We have studied the effect of SK&F 107461 (a hydroxyethylene dipeptide isostere inhibitor of HIV protease), on various host defense functions of human monocytes [6].
Studies of human immunodeficiency virus type 1 (HIV-1) protease inhibitors. III. Structure-activity relationship of HIV-1 protease inhibitors containing cyclohexylalanylalanine hydroxyethylene dipeptide isostere [7].

Biological context of AIDS006007

Kinetics of the inhibition of human renin by an inhibitor containing a hydroxyethylene dipeptide isostere [8].

References

L-685,458, an aspartyl protease transition state mimic, is a potent inhibitor of amyloid beta-protein precursor gamma-secretase activity. Shearman, M.S., Beher, D., Clarke, E.E., Lewis, H.D., Harrison, T., Hunt, P., Nadin, A., Smith, A.L., Stevenson, G., Castro, J.L. Biochemistry (2000) [Pubmed]
An efficient, stereoselective synthesis of the hydroxyethylene dipeptide isostere core for the HIV protease inhibitor A-792611. Engstrom, K., Henry, R., Hollis, L.S., Kotecki, B., Marsden, I., Pu, Y.M., Wagaw, S., Wang, W. J. Org. Chem. (2006) [Pubmed]
Linear non-competitive inhibition of solubilized human gamma-secretase by pepstatin A methylester, L685458, sulfonamides, and benzodiazepines. Tian, G., Sobotka-Briner, C.D., Zysk, J., Liu, X., Birr, C., Sylvester, M.A., Edwards, P.D., Scott, C.D., Greenberg, B.D. J. Biol. Chem. (2002) [Pubmed]
Preorganization of the hydroxyethylene dipeptide isostere: the preferred conformation in solution resembles the conformation bound to BACE. Vidal, P., Timm, D., Broughton, H., Chen, S.H., Martín, J.A., Rivera-Sagredo, A., McCarthy, J.R., Shapiro, M.J., Espinosa, J.F. J. Med. Chem. (2005) [Pubmed]
Renin inhibitors based on dipeptide analogues. Incorporation of the hydroxyethylene isostere at the P2/P3 sites. Kempf, D.J., de Lara, E., Stein, H.H., Cohen, J., Egan, D.A., Plattner, J.J. J. Med. Chem. (1990) [Pubmed]
Effect of a human immunodeficiency virus protease inhibitor on human monocyte function. Bugelski, P.J., Kaplan, J.M., Hart, T.K., Miller, J., Laydon, J.T., Lee, J.C., Dreyer, G.B., Kirsh, R. AIDS Res. Hum. Retroviruses (1992) [Pubmed]
Studies of human immunodeficiency virus type 1 (HIV-1) protease inhibitors. III. Structure-activity relationship of HIV-1 protease inhibitors containing cyclohexylalanylalanine hydroxyethylene dipeptide isostere. Sakurai, M., Higashida, S., Sugano, M., Handa, H., Komai, T., Yagi, R., Nishigaki, T., Yabe, Y. Chem. Pharm. Bull. (1994) [Pubmed]
Kinetics of the inhibition of human renin by an inhibitor containing a hydroxyethylene dipeptide isostere. Kati, W.M., Pals, D.T., Thaisrivongs, S. Biochemistry (1987) [Pubmed]

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