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913588

Sigma-Aldrich

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

≥95%

Synonyme(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

Formule empirique (notation de Hill):
C16H17ClN2O5
Numéro CAS:
207727-86-4
Poids moléculaire :
352.77
Numéro MDL:
MFCD16495886
Code UNSPSC :
12352209

Pureté

≥95%

Forme

powder

Disponibilité

available only in USA

Pf

205 °C (decomp.)

Température de stockage

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

Clé InChI

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)

Autres remarques

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

N7389

3-Nitro-L-tyrosine, crystalline

14010

O-Benzyl-L-tyrosine, ≥99.0% (NT)

47751

Fmoc-Tyr-OH, ≥97.0% (HPLC)

374229

Boc-Tyr-OH, 98%

902314

[CpRu(Fmoc-tyrosin)]CF3CO2

8.52058

Fmoc-Tyr(PO₃H₂)-OH, Novabiochem®

8.53043

Boc-Tyr-OH, Novabiochem®

8.52051

Fmoc-Tyr-OH, Novabiochem®

914339

Fmoc-L-Lys(Nvoc)-OH, ≥98%

914525

o-Nitropiperonyl-O-tyrosine

915793

Methyl-o-nitropiperonyllysine, ≥95%

Pictogrammes

Flame
GHS02

Mention d'avertissement

Danger

Mentions de danger

H242

Classification des risques

Self-react. C

Code de la classe de stockage

5.2 - Organic peroxides and self-reacting hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Lei Wang et al.
Angewandte Chemie (International ed. in English), 44(1), 34-66 (2004-12-16)
Although chemists can synthesize virtually any small organic molecule, our ability to rationally manipulate the structures of proteins is quite limited, despite their involvement in virtually every life process. For most proteins, modifications are largely restricted to substitutions among the
Jana K Böcker et al.
Angewandte Chemie (International ed. in English), 54(7), 2116-2120 (2015-01-06)
Cyclic peptides are important natural products and hold great promise for the identification of new bioactive molecules. The split-intein-mediated SICLOPPS technology provides a generic access to fully genetically encoded head-to-tail cyclized peptides and large libraries thereof (SICLOPPS=split-intein circular ligation of
Light-activated gene editing with a photocaged zinc-finger nuclease.
Chungjung Chou et al.
Angewandte Chemie (International ed. in English), 50(30), 6839-6842 (2011-06-15)
Evolution of amber suppressor tRNAs for efficient bacterial production of proteins containing nonnatural amino acids.
Jiantao Guo et al.
Angewandte Chemie (International ed. in English), 48(48), 9148-9151 (2009-10-27)
Thomas Bridge et al.
Angewandte Chemie (International ed. in English), 58(50), 17986-17993 (2019-10-15)
Antibodies have found applications in several fields, including, medicine, diagnostics, and nanotechnology, yet methods to modulate antibody-antigen binding using an external agent remain limited. Here, we have developed photoactive antibody fragments by genetic site-specific replacement of single tyrosine residues with
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