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907391

Sigma-Aldrich

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:
1360651-24-6
Molecular Weight:
365.38
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

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)

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

907391-VAR:
907391-50MG:
907391-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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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