L-685, 458

  • CAT Number: I003019
  • CAS Number: 292632-98-5
  • Molecular Formula: C₃₉H₅₂N₄O₆
  • Molecular Weight: 672.85
  • Purity: ≥95%
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L-685,458(Cat No.:I003019) is a compound that acts as a highly specific and potent inhibitor of beta PP gamma-secretase activity. It has a Ki value of 17 nM, meaning that it can bind tightly to and effectively block the activity of this enzyme, which is involved in the production of amyloid beta peptides in Alzheimer’s disease. By inhibiting beta PP gamma-secretase activity, L-685,458 can potentially reduce the accumulation of these peptides in the brain and delay the progression of Alzheimer’s disease.


Catalog Number I003019
CAS Number 292632-98-5
Synonyms

tert-butyl N-[(2S,3R,5R)-6-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate

Molecular Formula C₃₉H₅₂N₄O₆
Purity ≥95%
Target Gamma Secretase
Solubility DMSO: ≥ 31 mg/mL
Storage Store at -20°C
IC50 17 nM
IUPAC Name tert-butyl N-[(2S,3R,5R)-6-[[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-benzyl-3-hydroxy-6-oxo-1-phenylhexan-2-yl]carbamate
InChI InChI=1S/C39H52N4O6/c1-26(2)21-33(37(47)41-32(35(40)45)24-29-19-13-8-14-20-29)42-36(46)30(22-27-15-9-6-10-16-27)25-34(44)31(23-28-17-11-7-12-18-28)43-38(48)49-39(3,4)5/h6-20,26,30-34,44H,21-25H2,1-5H3,(H2,40,45)(H,41,47)(H,42,46)(H,43,48)/t30-,31-,32-,33-
InChIKey MURCDOXDAHPNRQ-PJRHAEEISA-N
SMILES CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)N)NC(=O)C(CC2=CC=CC=C2)CC(C(CC3=CC=CC=C3)NC(=O)OC(C)(C)C)O
Reference

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<br>[1]. Shearman MS, et al. L-685,458, an aspartyl protease transition state mimic, is a potent inhibitor of amyloid beta-protein precursor gamma-secretase activity. Biochemistry. 2000 Aug 1;39(30):8698-8704.
<br>[2]. Zhang P, et al. Biological significance and therapeutic implication of resveratrol-inhibited Wnt, Notch and STAT3 signaling in cervical cancer cells. Genes Cancer. 2014 May;5(5-6):154-164.
<br>[3]. Jeon JH, et al. Glucosamine-induced OGT activation mediates glucose production through cleaved Notch1 and FoxO1, which coordinately contributed to the regulation of maintenance of self-renewal in mouse embryonic stem cells. Stem Cells Dev. 2014 Sep 1;23(17):2067-2079.
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