16874-12-7

Basic information

• Product Name: tert-Butyl L-tyrosinate
• Synonyms: tert-butyl l-tyrosinate;TYROSINE-OTBU;H-TYR-OBUT;H-TYR-OTBU;L-TYROSINE T-BUTYL ESTER;L-TYROSINE TERT-BUTYL ESTER;2-Amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester;Tyr-OtBu
• CAS NO: 16874-12-7
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.29
• EINECS: 240-902-3
• Product Categories: chiral;Miscellaneous;Amino Acids;Tyrosine [Tyr, Y];Amino Acids and Derivatives;Amino Acid tert-Butyl Esters;Amino Acids (C-Protected);Biochemistry;Amino ester;Amino Acid Derivatives;Amino Acids;I - ZPeptide Synthesis;Modified Amino Acids;Tyrosine
• Mol File: 16874-12-7.mol

Chemical Properties

• Melting Point: 141-144 °C
• Boiling Point: 358.1 °C at 760 mmHg
• Flash Point: 170.4 °C
• Appearance: White/Powder
• Density: 1.125 g/cm³
• Vapor Pressure: 1.26E-05mmHg at 25°C
• Refractive Index: 25 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 9.80±0.15(Predicted)
• BRN: 2696011
• CAS DataBase Reference: tert-Butyl L-tyrosinate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl L-tyrosinate(16874-12-7)
• EPA Substance Registry System: tert-Butyl L-tyrosinate(16874-12-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 16874-12-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
t-Butyl L-tyrosinate is used as a precursor for the synthesis of catecholamines, such as Norepinephrine HCl, which play a vital role in the human body's response to stress and are involved in various physiological processes. This application is particularly relevant in the development of treatments for conditions related to the sympathetic nervous system.
Used in Protein Synthesis:
t-Butyl L-tyrosinate is utilized as a building block in the synthesis of proteins, which are essential macromolecules that perform a wide range of functions in living organisms. The incorporation of this amino acid ester into proteins can contribute to their structure, stability, and function.
Used in Thyroid Hormone Synthesis:
t-Butyl L-tyrosinate is also used as a precursor in the production of thyroid hormones, which are critical for regulating metabolism, growth, and development in the human body. The synthesis of these hormones using t-Butyl L-tyrosinate can be beneficial in the treatment of thyroid-related disorders and maintaining overall health.
Used in Antioxidant and Antiradical Applications:
Due to its in vitro antioxidant and antiradical properties, t-Butyl L-tyrosinate can be employed in the development of compounds that protect cells from oxidative stress and damage. This application can be particularly useful in the fields of nutrition, cosmetics, and pharmaceuticals, where the prevention of oxidative damage is of significant importance.

InChI:InChI=1/C13H19NO3/c1-13(2,3)17-12(16)11(14)8-9-4-6-10(15)7-5-9/h4-7,11,15H,8,14H2,1-3H3/t11-/m0/s1

Upstream product

• 60-18-4 L-tyrosine 
• 115-11-7 isobutene 
• 16881-33-7 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate 
• 217172-40-2 (S)-2-amino-3-(4-benzyloxy-phenyl)-tert-butyl-propionic ester 
• 5544-60-5 4-(benzyloxy)benzyl bromide 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 1027921-22-7 2-(benzhydrylidene-amino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester 
• 1164-16-5 Z-L-Tyr-OH 
• 540-88-5 acetic acid tert-butyl ester 
• 88878-78-8 tyrosine tert-butyl ester 
• 67-56-1 methanol 
• 112883-29-1 N-Fmoc-Tyr-OH 
• 133852-23-0 tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate 

Downstream Products

• 18938-60-8 (S)-tert-butyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate 
• 142822-20-6 N-benzyloxycarbonyl-L-seryl-L-tyrosine tert-butyl ester 
• 60-18-4 L-tyrosine 
• 179188-06-8 N-benzyltyrosine tert-butyl ester 
• 192822-99-4 N,N-dibenzyltyrosine tert-butyl ester 
• 133852-23-0 tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate 
• 178271-91-5 (S)-2-Benzyloxycarbonylamino-N-[(S)-1-tert-butoxycarbonyl-2-(4-hydroxy-phenyl)-ethyl]-succinamic acid benzyl ester 
• 222976-52-5 2-tert-butoxycarbonylamino-N-[1-tert-butoxycarbonyl-2-(4-hydroxy-phenyl)-ethyl]-malonamic acid methyl ester 
• 185062-85-5 nitroveratryloxycarbonyl-L-tyrosine t-butyl ester 
• 221077-12-9 benzyl 4-{[(1S)-2-(tert-butoxy)-1-(4-hydroxybenzyl)-2-oxoethyl]amino}-4-oxobutanoate 
• 432515-20-3 (S)-t-butyl 3-(4-hydroxyphenyl)-2-(3-trifluoromethylbenzenesulfonylamino)propionate 
• 432515-18-9 3-(4-hydroxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester 
• 67932-53-0 5,7-dinitroindoline 
• 16881-33-7 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate 

Relevant articles and documents

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

Synthesis and anticancer activities of proline-containing cyclic peptides and their linear analogs and congeners

A solution phase method was adopted for the synthesis of proline-containing cyclic pentapeptide 2 and total synthesis of naturally occurring cyclic heptapeptide Reniochalistatin B 3. For the synthesis of 3, both divergent and convergent strategies were used to improve the overall yield from 12 to 25%. Different N and C terminal modified linear analogs and congeners of 2 and 3 were synthesized. Both cyclic peptides 2 and 3 and their linear analogs/congeners were evaluated for anti-cancer activity against HeLa cell line, among which pentapeptide 2 h and hexapeptide 3n with N-terminal protected hexafluoroisopropyl carbamates (HFIPC) interestingly showed higher cytotoxicity with an IC50 of 2.73 and 4.3 μM, respectively compared to their Boc-protected analogs 2a (IC50 20 μM) and 3c (IC50 38.51 μM) and cyclic peptides 2 (>100 μM) and 3 (47 μM). These results were further validated by biological experiments such as colony formation and wound healing assays.

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

Base/Cryptand/Metal-Free Automated Nucleophilic Radiofluorination of [18F]FDOPA from Iodonium Salts: Importance of Hydrogen Carbonate Counterion

As evidenced by the number of publications and patents published in the last years, the radiosynthesis of 6-[18F]fluoro-3,4-dihydroxy-L-phenylalanine ([18F]FDOPA) using the nucleophilic [18F]F- process remains currently a challenge for the radiochemists scientific community even if promising methods for the radiofluorination of electron-rich aromatic structures were recently developed from arylboronate, arylstannane or iodonium salt precursors. In such context, based on the use of an iodonium triflate salt precursor, we optimized a fast and efficient radiofluorination route fully automated and free from any base, cryptand or metal catalyst for the radiosynthesis of [18F]FDOPA. Using this method, this clinically relevant radiotracer was produced in 64 min, 27–38 % RCY d.c. (n = 5), >99 % RCP, >99 % ee., and high Am 170–230 GBq/μmol. In addition, this optimization study clearly highlighted the important role of a triflate-hydrogen carbonate counterion exchange during the radiolabeling process to achieve high fluorine-18 incorporation yields.

A novel SWCNT platform bearing DOTA and β-cyclodextrin units. "one shot" multidecoration under microwave irradiation

The functionalization of single-walled carbon nanotubes (SWCNTs) via microwave-assisted grafting reactions enables efficient multidecoration in a single step. A novel water-soluble SWCNT platform was prepared via the simple 1,3-dipolar cycloaddition of azomethine ylides under dielectric heating. Thanks to a single grafting reaction the CNT surface binds in a 1:1 ratio an amino acidic β-cyclodextrin (β-CD) derivative and the DOTAMA moiety (1,4,7,10-tetraazacyclododecane-N,N′,N′′,N′′ ′-tetraacetic acid monoamide). This novel "one shot" synthesis, compared with multistep functionalizations, preserves the SWCNT's structural integrity (TEM images). Besides thermogravimetric analyses, the determination of the amount of β-CD and DOTA moieties grafting onto the SWCNT's surface was performed on the basis of phenolphthalein and gadolinium complexation, respectively. This journal is

MODULATORS OF TLR3/DSRNA COMPLEX AND USES THEREOF

The present invention provides compounds and compositions that can modulate formation of Toll-like receptor 3 (TLR3) and double-stranded RNA (dsRNA) complex, and methods for using the same. In particular, some aspects of the invention provide compounds of the formula (I) compositions comprising and methods for using the same, where n, Ar1, Ar2, X1, X2, X3, Z1, and Z2 are those defined herein.

Small-molecule inhibitors of the TLR3/dsRNA complex

The protein-RNA interface has been regarded as "undruggable" despite its importance in many biological processes. The toll-like receptor 3 (TLR3)/double-stranded RNA (dsRNA) complex provides an exciting target for a number of infectious diseases and cancers. We describe the development of a series of small-molecule probes that were shown to be competitive inhibitors of dsRNA binding to TLR3 with high affinity and specificity. In a multitude of assays, compound 4a was profiled as a potent antagonist to TLR3 signaling and also repressed the expression of downstream signaling pathways mediated by the TLR3/dsRNA complex, including TNF-α and IL-1β.

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

αvβ3 integrin-targeting Arg-Gly-Asp (RGD) peptidomimetics containing oligoethylene glycol (OEG) spacers

RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting αvβ3 integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human αvβ 3 integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin αIIbβ3. Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved. 2009 American Chemical Society.

Design of new, chiral phase-transfer catalysts for practical, catalytic asymmetric synthesis

Structurally rigid, chiral spiro ammonium salts of type 1 derived from commercially available (S)-binaphthol have been designed as a new C2-symmetric chiral phase-transfer catalyst and successfully applied to the highly efficient, catalytic enantioselective alkylation of tert-butyl glycinate Schiff base under mild phase-transfer conditions to furnish a-alkyl-oc-amino acids and α,α-dialkyl-α-amino acids with excellent enantioselectivity. These ammonium salts have been also utilized for the in situ generation of chiral quaternary ammonium fluorides.