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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:
Molecular Weight:
352.77
MDL number:
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)

pictograms

Flame

signalword

Danger

hcodes

Hazard Classifications

Self-react. C

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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