34996-91-3

Basic information

• Product Name: N-benzoyltyrosine
• Synonyms: 34996-91-3; N-Benzoyltyrosine; QR D1YVQMVR; tyrosine, N-benzoyl-
• CAS NO: 34996-91-3
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.2946
• Mol File: 34996-91-3.mol
• Article Data: 31

Chemical Properties

• Boiling Point: 598.2°C at 760 mmHg
• Flash Point: 315.6°C
• Density: 1.315g/cm³
• Vapor Pressure: 3.72E-15mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: N-benzoyltyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzoyltyrosine(34996-91-3)
• EPA Substance Registry System: N-benzoyltyrosine(34996-91-3)

Safety Data

• Hazardous Substances Data: 34996-91-3(Hazardous Substances Data)

Upstream product

• 6154-45-6 BzTyr-p-nitroanilide 
• 58690-81-6 Bz-Tyr-NH₂ 
• 10418-01-6 N-benzoyl-L-tyrosine methyl ester 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 556-02-5 ?Tyr 
• 82301-52-8 (Z)-4-(4-hydroxybenzylidene)-2-phenyloxazolin-5(4H)-one 
• 25713-45-5 N-(1-(4-nitrophenylcarbamoyl)-2-(4-hydroxyphenyl)ethyl) benzamide 
• 3417-91-2 tyrosine methyl ester hydrochloride 
• 4276-17-9 methyl (N-benzoyl)-4'-hydroxyphenylalaninate 
• 97485-13-7 2-benzamido-3-(4-(benzoyloxy)phenyl)propanoic acid 
• 32089-82-0 2-benzoylamino-3-(4-hydroxy-phenyl)-acrylic acid 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 60-18-4 L-tyrosine 

Downstream Products

• 6154-45-6 BzTyr-p-nitroanilide 
• 556-02-5 ?Tyr 
• 65-85-0 benzoic acid 
• 934221-21-3 N-(N-benzoyl-L-tyrosyl)-L-phenylalanine methyl ester 
• 934221-17-7 N-(N-benzoyl-6-nitro-l-tyrosyl)-L-phenylalanine methyl ester 
• 934221-81-5 sodium N-(N-benzoyl-L-tyrosyl)-7-acetamido-L-phenylalaninate 
• 59921-69-6 3-nitro-N-benzoyl-L-tyrosine 
• 1627753-34-7 C₂₈H₂₉N₃O₆ 
• 1627753-30-3 C₂₅H₂₅N₃O₆ 
• 1627753-32-5 C₂₆H₂₅N₃O₇ 

Relevant articles and documents

Protein Modification at Tyrosine with Iminoxyl Radicals

Post-translational modifications (PTMs) of proteins are a biological mechanism for reversibly controlling protein function. Synthetic protein modifications (SPMs) at specific canonical amino acids can mimic PTMs. However, reversible SPMs at hydrophobic amino acid residues in proteins are especially limited. Here, we report a tyrosine (Tyr)-selective SPM utilizing persistent iminoxyl radicals, which are readily generated from sterically hindered oximes via single-electron oxidation. The reactivity of iminoxyl radicals with Tyr was dependent on the steric and electronic demands of oximes; isopropyl methyl piperidinium oxime 1f formed stable adducts, whereas the reaction of tert-butyl methyl piperidinium oxime 1o was reversible. The difference in reversibility between 1f and 1o, differentiated only by one methyl group, is due to the stability of iminoxyl radicals, which is partly dictated by the bond dissociation energy of oxime O-H groups. The Tyr-selective modifications with 1f and 1o proceeded under physiologically relevant, mild conditions. Specifically, the stable Tyr-modification with 1f introduced functional small molecules, including an azobenzene photoswitch, to proteins. Moreover, masking critical Tyr residues by SPM with 1o, and subsequent deconjugation triggered by the treatment with a thiol, enabled on-demand control of protein functions. We applied this reversible Tyr modification with 1o to alter an enzymatic activity and the binding affinity of a monoclonal antibody with an antigen upon modification/deconjugation. The on-demand ON/OFF switch of protein functions through Tyr-selective and reversible covalent-bond formation will provide unique opportunities in biological research and therapeutics.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

Efficient Synthesis of Glycosylated Matijin-Su Derivatives via Ultrasonic Irradiation

Matijin-Su (1) is a phenylalanine dipeptide compound with anti-hepatitis B virus (HBV) activity. Previous reports suggest that the synthesis of glycosylated Matijin-Su derivatives needs at least 10 steps. To simplify the synthetic procedure, we have developed a shorter and more efficient method for the preparation via ultrasound irradiation. Two galactopyranosylated (2) and two glucopyranosylated (3) derivatives were synthesized in 6 or 7 steps. The overall yields for the total synthesis of galactopyranosylated derivatives were markedly increased to 39% (2a) or 22% (2b). And the yields for glucopyranosylated derivatives also reached 29% (3a) or 16% (3b).