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913588

Sigma-Aldrich

O-(2-Nitrobenzyl)-L-tyrosine hydrochloride

≥95%

Synonym(s):

(S)-2-Amino-3-(4-((2-nitrobenzyl)oxy)phenyl)propanoic acid hydrochloride, NBY, ONBY, Photo-controlled amino acid, Photocaged amino acid, Photocleavable tyrosine derivative

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About This Item

Empirical Formula (Hill Notation):
C16H17ClN2O5
CAS Number:
207727-86-4
Molecular Weight:
352.77
MDL number:
MFCD16495886
UNSPSC Code:
12352209

Assay

≥95%

form

powder

availability

available only in USA

mp

205 °C (decomp.)

storage temp.

2-8°C

InChI

1S/C16H16N2O5.ClH/c17-14(16(19)20)9-11-5-7-13(8-6-11)23-10-12-3-1-2-4-15(12)18(21)22;/h1-8,14H,9-10,17H2,(H,19,20);1H/t14-;/m0./s1

InChI key

DRUCEARMIBXBOJ-UQKRIMTDSA-N

Application

O-(2-Nitrobenzyl)-L-tyrosine hydrochloride (NBY) is a tyrosine derivative with an o-nitrobenzyl photocage that can be cleaved with 365 nm irradiation. NBY has been genetically encoded into multiple proteins, providing an ″on switch″ for regulation. Photocaged amino acids such as these are also useful in the synthesis of photocleavable chemical tools for spatial and temporal control over released molecules in biological applications.

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

Other Notes

Site-Specific Encoding of Photoactivity in Antibodies Enables Light-Mediated Antibody-Antigen Binding on Live Cells

Time-resolved protein activation by proximal decaging in living systems

Crystal structure of a domain-swapped photoactivatable sfGFP variant provides evidence for GFP folding pathway

Light-control of the ultra-fast Gp41-1 split intein with preserved stability of a genetically encoded photo-caged amino acid in bacterial cells

Rapid and Inexpensive Evaluation of Nonstandard Amino Acid Incorporation in Escherichia coli

related product

Product No.
Description
Pricing

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H242

Hazard Classifications

Self-react. C

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Susan E Cellitti et al.
Journal of the American Chemical Society, 130(29), 9268-9281 (2008-06-26)
In vivo incorporation of isotopically labeled unnatural amino acids into large proteins drastically reduces the complexity of nuclear magnetic resonance (NMR) spectra. Incorporation is accomplished by coexpressing an orthogonal tRNA/aminoacyl-tRNA synthetase pair specific for the unnatural amino acid added to
J Luo et al.
Chemical communications (Cambridge, England), 52(55), 8529-8532 (2016-06-10)
We developed two tightly regulated, light-activated Cre recombinase enzymes through site-specific incorporation of two genetically-encoded photocaged amino acids in human cells. Excellent optical off to on switching of DNA recombination was achieved. Furthermore, we demonstrated precise spatial control of Cre

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