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L1790

L-685,458

Name: L-685,458
Brand: SIGMA

>96% (HPLC), solid

Synonym(s):

(5S)-(t-Butoxycarbonylamino)-6-phenyl-(4R)hydroxy-(2R)benzylhexanoyl)-L-leu-L-phe-amide

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About This Item

Empirical Formula (Hill Notation):

C₃₉H₅₂O₆N₄

CAS Number:

292632-98-5

Molecular Weight:

672.85

NACRES:

NA.77

PubChem Substance ID:

329817393

UNSPSC Code:

12352200

MDL number:

MFCD03093402

Assay:

>96% (HPLC)

Form:

solid

Quality level:

100

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Properties

Quality Level

100

assay

>96% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

storage temp.

−20°C

SMILES string

O[C@@H]([C@H](CC1=CC=CC=C1)NC(OC(C)(C)C)=O)C[C@@H](CC2=CC=CC=C2)C(N[C@@H](CC(C)C)C(N[C@@H](CC3=CC=CC=C3)C(N)=O)=O)=O

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+,34-/m1/s1

InChI key

MURCDOXDAHPNRQ-ZJKZPDEISA-N

Gene Information

Description

Application

L-685,458 has been used to attenuate Notch signalling in ovary culture. It has also been used to analyze the specificity of the γ-secretase activity in brain tissue samples.

Biochem/physiol Actions

L-685,458 is a potent, selective, structurally novel γ-secretase inhibitor; equipotent inhibitor of both Aβ_1-42 and Aβ_1-40 production.

L-685,458 mimics the transition state in aspartyl protease. It possesses an IC50 of 17nM with respect to inhibition of Aβ synthesis. It is known to block Notch (neurogenic locus notch homolog protein) signaling, which in turn reduces ERK (extracellular signal regulated kinase) phosphorylation by EGF (epidermal growth factor). L-685,458 targets the active site and substrate binding site of the enzyme.

Features and Benefits

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

Manufactured and sold under license from Merck & Co., Inc., Kenilworth, NJ, U.S.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Regulation of primordial follicle recruitment by cross-talk between the Notch and phosphatase and tensin homologue (PTEN)/AKT pathways

Wang LQ, et al.

Reproductive Biology and Endocrinology, 28(6), 700-712 (2016)

C-terminal fragment of presenilin is the molecular target of a dipeptidic gamma-secretase-specific inhibitor DAPT (N-[N-(3, 5-difluorophenacetyl)-l-alanyl]-S-phenylglycine t-butyl ester)

Morohashi Y, et al.

The Journal of biological chemistry, 281(21), 14670-14676 (2006)

Effects of Alzheimer's disease-associated risk loci on cerebrospinal fluid biomarkers and disease progression: a polygenic risk score approach

Martiskainen H, et al.

Journal of Alzheimer'S Disease, 43(2), 565-573 (2015)

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