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Merck
CN

907367

Fmoc-L-photo-methionine

≥95%, for peptide synthesis

Synonym(s):

(S)-2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-4-(3-methyl-3H-diazirin-3-yl)butanoic acid, (S)-2-(Fmoc-amino)-4-(3H-diazirin-3-yl)pentanoic acid, Diazirine amino acid, Photo-Met, Photo-crosslinking amino acid, Photoprobe building block

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About This Item

Empirical Formula (Hill Notation):
C21H21N3O4
CAS Number:
945859-89-2
Molecular Weight:
379.41
MDL number:
MFCD31380717
UNSPSC Code:
12352209
NACRES:
NA.22

Key Documents

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Product Name

Fmoc-L-photo-methionine, ≥95%

InChI key

QKMQUEIDJLPYHS-SFHVURJKSA-N

SMILES string

N([C@@H](CCC4(N=N4)C)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3

assay

≥95%

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

−20°C

Related Categories

Application

Fmoc-L-photo-methionine is a diazirine-containing, Fmoc-protected methionine amino acid and multifunctional photo-crosslinker. Its incorporation into peptides or small-molecule probes and tools allows for photoaffinity labeling of cellular targets and protein-protein interactions upon UV light (∼360 nm) irradiation to form a covalent bond. This and other multifunctional probe building blocks will continue to accelerate drug discovery research for probing cellular mechanisms, target ID/validation, and understanding traditionally undruggable targets. An unprotected version is also available as 907375.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

Developing diazirine-based chemical probes to identify histone modification ′readers′ and ′erasers ′

Proteome profiling reveals potential cellular targets of staurosporine using a clickable cell-permeable probe

Covalent Capture of Phospho-Dependent Protein Oligomerization by Site-Specific Incorporation of a Diazirine Photo-Cross-Linker

Fishing for Drug Targets: A Focus on Diazirine Photoaffinity Probe Synthesis

Photo-affinity labeling (PAL) in chemical proteomics: a handy tool to investigate protein-protein interactions (PPIs)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT7642
MKCQ4980

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Covalent capture of phospho-dependent protein oligomerization by site-specific incorporation of a diazirine photo-cross-linker.
Miquel Vila-Perelló et al.
Journal of the American Chemical Society, 129(26), 8068-8069 (2007-06-15)
Haibin Shi et al.
Chemical communications (Cambridge, England), 47(40), 11306-11308 (2011-09-17)
A clickable, affinity-based probe (AfBP), which was modified from staurosporine (a natural product kinase inhibitor), has been synthesized and used in situ for activity-based proteome profiling of potential cellular targets of staurosporine in HepG2 cancer cells.
Tangpo Yang et al.
Chemical science, 6(2), 1011-1017 (2015-02-01)
Post translational modifications (PTMs, e.g., phosphorylation, acetylation and methylation) of histone play important roles in regulating many fundamental cellular processes such as gene transcription, DNA replication and damage repair. While 'writer' and 'eraser' enzymes modify histones by catalyzing the addition

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