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907391

Sigma-Aldrich

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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About This Item

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

Essai

≥98%

Forme

powder

Capacité de réaction

reaction type: Fmoc solid-phase peptide synthesis

Application(s)

peptide synthesis

Groupe fonctionnel

Fmoc

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

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)

Autres remarques

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)

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

907294

Fmoc-L-Photo-Phe-OH, ≥95%

907324

Fmoc-L-photo-proline, ≥95%

907251

H-L-Photo-lysine HCl, ≥98%

907278

H-L-Photo-leucine HCl, ≥98%

907286

H-L-Photo-Proline hydrochloride, ≥95%

907340

H-L-Photo-Phe-OH, ≥98%

907367

Fmoc-L-photo-methionine, ≥95%

907375

H-L-Photo-methionine HCl, ≥95%

907383

Fmoc-L-Photo-Lysine, ≥95%

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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)
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
En-Wei Lin et al.
Bioconjugate chemistry, 25(10), 1902-1909 (2014-10-16)
A photoactivated, site-selective conjugation of poly(ethylene glycol) (PEG) to the glutathione (GSH) binding pocket of glutathione S-transferase (GST) is described. To achieve this, a GSH analogue (GSH-BP) was designed and chemically synthesized with three functionalities: (1) the binding affinity of

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