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912182

Sigma-Aldrich

Enantioprobe (S,S)-7

≥95%

Synonym(s):

N-((1S,2S)-2-(Benzyloxy)cyclopentyl)-3-(3-(but-3-yn-1-yl)-3H-diazirin-3-yl)propanamide, Fully functionalized enantioprobe, Ligandability probe

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About This Item

Empirical Formula (Hill Notation):
C20H25N3O2
CAS Number:
Molecular Weight:
339.43
UNSPSC Code:
12352101
NACRES:
NA.22

Quality Level

Assay

≥95%

form

powder

storage temp.

−20°C

Application

Enantioprobe (S,S)-7 is one of 16 fully functionalized, enantiomeric fragment probes developed in the Cravatt lab. Combining fragment-based ligand discovery (FBLD) with chemical proteomics, the enantioprobe library assesses ligandability across proteomes. Each enantioprobe contains a structurally variable fragment for interaction with proteins, photoactivatable diazirine for UV-induced covalent protein labeling, and bioorthogonal alkyne handle for detection, enrichment, and identification. Of the eight enantiomeric pairs, each differs by one stereocenter, and comparing stereoselective fragment-protein interactions betweenthe pairs simplifies validation of authentic protein-binding events. Enantioprobe (S,S)-7′s paired fragment is available as Enantioprobe (R,R)-7 (cat# 913413).

Together, the 16 enantioprobes support ligandability studies in living cells, a significant method for development of chemical probes and lead discovery efforts to find binders for traditionally ″″undruggable″″ protein targets. This strategy is also compatible with multiplexing for higher throughput.
Supporting reagents:

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Yujia Wang et al.
Nature chemistry, 11(12), 1113-1123 (2019-10-30)
A fundamental challenge in chemical biology and medicine is to understand and expand the fraction of the human proteome that can be targeted by small molecules. We recently described a strategy that integrates fragment-based ligand discovery with chemical proteomics to

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