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907391

Fmoc-L-photo-leucine

≥98%

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C20H19N3O4
Numéro CAS:
1360651-24-6
Poids moléculaire :
365.38
MDL number:
MFCD31380715
UNSPSC Code:
12352209
NACRES:
NA.22
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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)

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)

Classe de stockage

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)
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Numéro d'article de commerce international

RéférenceGTIN
907391-50MG04022536044941