907391
Fmoc-L-photo-leucine
≥98%
Synonym(s):
(S)-2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-3-(3-methyl-3H-diazirin-3-yl)propanoic acid, (S)-2-(Fmoc-amino)-3-(3H-diazirin-3-yl)butanoic acid, Photo-Leu, Photo-crosslinking amino acid, Photoprobe building block
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About This Item
Empirical Formula (Hill Notation):
C20H19N3O4
CAS Number:
Molecular Weight:
365.38
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22
assay
≥98%
form
powder
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
application(s)
peptide synthesis
functional group
Fmoc
storage temp.
2-8°C
SMILES string
N([C@@H](CC4(N=N4)C)C(=O)O)C(=O)OCC1c2c(cccc2)c3c1cccc3
InChI
1S/C20H19N3O4/c1-20(22-23-20)10-17(18(24)25)21-19(26)27-11-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,16-17H,10-11H2,1H3,(H,21,26)(H,24,25)/t17-/m0/s1
InChI key
GDWMJFRPAHGSDU-KRWDZBQOSA-N
Application
Fmoc-L-Photo-Leucine is a diazirine-containing, Fmoc-protected leucine 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 907278.
Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)
Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)
Other Notes
Synthesis of a polymyxin derivative for photolabeling studies in the gram-negative bacterium Escherichia coli
Developing diazirine-based chemical probes to identify histone modification ′readers′ and ′erasers′
Protein-Polymer Conjugation via Ligand Affinity and Photoactivation of Glutathione S-Transferase
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)
Developing diazirine-based chemical probes to identify histone modification ′readers′ and ′erasers′
Protein-Polymer Conjugation via Ligand Affinity and Photoactivation of Glutathione S-Transferase
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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Benjamin van der Meijden et al.
Journal of peptide science : an official publication of the European Peptide Society, 21(3), 231-235 (2015-02-03)
The antimicrobial activity of polymyxins against Gram-negative bacteria has been known for several decades, but the mechanism of action leading to cell death has not been fully explored. A key step after binding of the antibiotic to lipopolysaccharide (LPS) exposed
Aleš Marek et al.
Journal of the American Society for Mass Spectrometry, 25(5), 778-789 (2014-02-20)
Gas-phase dissociations were investigated for several peptide ions containing the Gly-Leu* N-terminal motif where Leu* was a modified norleucine residue containing the photolabile diazirine ring. Collisional activation of gas-phase peptide cations resulted in facile N₂ elimination that competed with backbone
Jay M Janz et al.
Journal of the American Chemical Society, 133(40), 15878-15881 (2011-09-13)
Cell surface heptahelical G protein-coupled receptors (GPCRs) mediate critical cellular signaling pathways and are important pharmaceutical drug targets. (1) In addition to traditional small-molecule approaches, lipopeptide-based GPCR-derived pepducins have emerged as a new class of pharmaceutical agents. (2, 3)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 907391-50MG | 04022536044941 |