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496000

Sigma-Aldrich

OM99-2

InSolution, ≥90%, analog inhibitor of human brain memapsin 2

Synonym(s):

InSolution OM99-2, EVNLΨAAEF

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About This Item

Empirical Formula (Hill Notation):
C41H64N8O14
CAS Number:
314266-76-7
Molecular Weight:
892.99
MDL number:
MFCD03452932
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥90% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
desiccated
protect from light

shipped in

ambient

storage temp.

−20°C

InChI

1S/C39H60N8O14/c1-18(2)12-24(43-36(57)25(16-29(41)49)45-38(59)32(19(3)4)47-35(56)23(40)15-30(50)51)28(48)13-20(5)33(54)42-21(6)34(55)44-26(17-31(52)53)37(58)46-27(39(60)61)14-22-10-8-7-9-11-22/h7-11,18-21,23-28,32,48H,12-17,40H2,1-6H3,(H2,41,49)(H,42,54)(H,43,57)(H,44,55)(H,45,59)(H,46,58)(H,47,56)(H,50,51)(H,52,53)(H,60,61)/t20-,21+,23+,24+,25+,26+,27+,28+,32+/m1/s1

InChI key

JCNFYXCBSRPSLY-QYTLZHMISA-N

General description

A peptidomimetic, highly potent, tight-binding transition-state analog inhibitor of human brain β-secretase (Ki = 1.6 nM, recombinant memapsin-2; Ki = 9.58 nM, recombinant pro-memapsin 2). Designed from the template of the β-secretase site of Swedish β-amyloid precursor protein (APP) with Asp to Ala replacement. Includes a nonhydrolyzable hydroxyethylene isostere between Leu and Ala. Also reported to inhibit cathepsin D at higher levels (Ki = 48 nM).
An eight residue peptidomimetic, tight binding transition-state analog inhibitor of human brain memapsin 2 (Ki = 1.6 nM, recombinant memapsin 2; Ki = 9.58 nM, recombinant pro-memapsin 2). Also inhibits cathepsin D (Ki = 48 nM). This aspartyl protease inhibitor is designed from the template of the β-secretase site of Swedish β-amyloid precursor protein (APP) with Asp to Ala replacement; also includes a nonhydrolyzable hydroxyethylene isostere between Leu and Ala.

Biochem/physiol Actions

Cell permeable: no
Primary Target
human brain memapsin 2
Product does not compete with ATP.
Reversible: no
Target Ki: 1.6 nM against recombinant memapsin 2; 9.58 nM against recombinant pro-memapsin 2; 48 nM against cathepsin D

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Sequence

Glu-Val-Asn-Leu-Ψ-Ala-Ala-Glu-Phe [Ψ denotes replacement of CONH by (S)-CH(OH)CH₂]

Physical form

A 1 mM (250µg in 280 µl) solution in DMSO. Supplied as a trifluoroacetate salt.

Reconstitution

Following initial thaw, aliquot and freeze (-20°C). Avoid freeze/thaw cycles of solutions.

Other Notes

Ghosh, A.K., et al. 2001. J. Med. Chem.44, 2865.
Turner III, R.T., et al. 2001. Biochemistry40, 10001.
Ghosh, A.K., et al. 2000. J. Am. Chem. Soc.122, 3522.
Hong, L., et al. 2000. Science290,150.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

wgk_germany

WGK 1

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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