3415-08-5

Basic information

• Product Name: H-TYR-NCA
• Synonyms: H-TYR-NCA;Tyrosine, NCA;N-Carboxy-L-tyrosine anhydride;(4S)-4-[(4-Hydroxyphenyl)methyl]-2,5-oxazolidinedione;L-Tyrosine N-carboxyanhydride;(2,5-Oxazolidinedione,4-[(4-hydroxyphenyl)Methyl]-, (4S)-;N-Carbonyl-L-Tyrosine Anhydride;L-Try-NCA
• CAS NO: 3415-08-5
• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.18276
• Product Categories: AMINOACIDS DERIVATIVES
• Mol File: 3415-08-5.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.423
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.14±0.40(Predicted)
• CAS DataBase Reference: H-TYR-NCA(CAS DataBase Reference)
• NIST Chemistry Reference: H-TYR-NCA(3415-08-5)
• EPA Substance Registry System: H-TYR-NCA(3415-08-5)

Safety Data

• Hazardous Substances Data: 3415-08-5(Hazardous Substances Data)

Usage

Description

H-TYR-NCA, also known as N-Carbonyl-L-tyrosine Anhydride, is an essential reactant used in the synthesis of various peptides. It plays a crucial role in the formation of peptide bonds, which are the building blocks of proteins. H-TYR-NCA is a versatile compound with applications in different industries due to its ability to contribute to the development of peptides with specific functions and properties.

Uses

Used in Pharmaceutical Industry:
H-TYR-NCA is used as a reactant for the synthesis of peptides, which are essential in the development of pharmaceutical products. One such peptide is glutamine penefit, which aids in optimum protein utilization for post-injury conditions. This application is particularly important for patients recovering from injuries or surgeries, as it helps in faster recovery and improved overall health.
Used in Research and Development:
In the field of research and development, H-TYR-NCA is used as a reactant to create novel peptides with potential therapeutic applications. These peptides can be designed to target specific biological pathways or interact with particular receptors, making them valuable tools in the development of new drugs and therapies.
Used in Cosmetics Industry:
H-TYR-NCA can also be utilized in the cosmetics industry for the synthesis of peptides with anti-aging, skin-repairing, and rejuvenating properties. These peptides can be incorporated into skincare products to enhance their effectiveness and provide consumers with improved skincare solutions.
Used in Agricultural Industry:
In agriculture, H-TYR-NCA can be employed in the development of bioactive peptides with potential applications in plant protection and growth promotion. These peptides can be used as natural alternatives to chemical pesticides and fertilizers, contributing to sustainable agricultural practices and reducing the environmental impact of farming.

Synthetic route

phosgene (75-44-5) + L-tyrosine (60-18-4) → L-tyrosine N-carboxyanhydride (3415-08-5)

Conditions	Yield
In tetrahydrofuran at 45℃; for 2.5h; Inert atmosphere;	95.9%
In tetrahydrofuran at 40 - 45℃;
With 1,4-dioxane

bis(trichloromethyl) carbonate (32315-10-9) + L-tyrosine (60-18-4) → L-tyrosine N-carboxyanhydride (3415-08-5)

Conditions	Yield
In tetrahydrofuran Inert atmosphere;	76.4%
In acetonitrile at 60℃; for 3h; Inert atmosphere;	70%
In acetonitrile at 70℃; for 4h; Inert atmosphere;	61.3%
In tetrahydrofuran at 45℃; for 6h;

chloroform (67-66-3) + L-tyrosine (60-18-4) → L-tyrosine N-carboxyanhydride (3415-08-5)

Conditions	Yield
With oxygen In acetonitrile at 70℃; UV-irradiation;	60%

N-carbamoyl-L-tyrosine (90899-85-7) → L-tyrosine N-carboxyanhydride (3415-08-5)

Conditions	Yield
With oxygen; nitrogen(II) oxide

3,4-dihydro-2H-pyran (110-87-2) + L-tyrosine N-carboxyanhydride (3415-08-5) → (S)-4-(4-(R)-tetrahydropyran-2-yloxy-benzyl)-oxazolidine-2,5-dione (33043-66-2)

Conditions	Yield
With p-toluenesulfonyl chloride for 65h; Ambient temperature;

3,4-dihydro-2H-pyran (110-87-2) + L-tyrosine N-carboxyanhydride (3415-08-5) → (S)-4-(4-(S)-tetrahydropyran-2-yloxy-benzyl)-oxazolidine-2,5-dione (33043-65-1)

Conditions	Yield
With p-toluenesulfonyl chloride for 65h; Ambient temperature;

chloro-trimethyl-silane (75-77-4) + L-tyrosine N-carboxyanhydride (3415-08-5) → (S)-3-trimethylsilanyl-4-(4-trimethylsilanyloxy-benzyl)-oxazolidine-2,5-dione (34545-71-6)

Conditions	Yield
With triethylamine In tetrahydrofuran

L-tyrosine N-carboxyanhydride (3415-08-5) + N-benzyl(trimethylsilyl)amine (14856-79-2) → (S)-2-(3-Benzyl-ureido)-3-(4-hydroxy-phenyl)-propionic acid

Conditions	Yield
In tetrahydrofuran

L-tyrosine N-carboxyanhydride (3415-08-5) + acetyl chloride (75-36-5) → L-Tyr(OAc) NCA (23224-65-9)

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 5℃; for 0.5h;

L-tyrosine N-carboxyanhydride (3415-08-5) + Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride (42267-27-6) + L-alanine N-carboxyanhydride (2224-52-4) + 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4) → Reaxys ID: 12456240

Conditions	Yield
Stage #1: L-tyrosine N-carboxyanhydride; Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride; L-alanine N-carboxyanhydride; 5-benzyl L-glutamate N-carboxyanhydride In 1,4-dioxane for 0.0833333h; Stage #2: With diethylamine In 1,4-dioxane at 23 - 27℃; for 24h; Stage #3: L-alanine N-carboxyanhydride

L-tyrosine N-carboxyanhydride (3415-08-5) + Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride (42267-27-6) + L-alanine N-carboxyanhydride (2224-52-4) + 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4) → Reaxys ID: 11383288

Conditions	Yield
With diethylamine In tetrahydrofuran; diethylamine Product distribution / selectivity;
In 1,4-dioxane; diethylamine Product distribution / selectivity;

L-tyrosine N-carboxyanhydride (3415-08-5) + N-ε-tert-butyloxycarbonyl-L-lysine N-carboxyanhydride (27097-41-2, 33043-60-6) + L-alanine N-carboxyanhydride (2224-52-4) + 5-benzyl L-glutamate N-carboxyanhydride (3190-71-4) → Reaxys ID: 11383656

Conditions	Yield
With diethylamine In 1,4-dioxane; diethylamine Product distribution / selectivity;

Upstream product

• 75-44-5 phosgene 
• 60-18-4 L-tyrosine 
• 90899-85-7 N-carbamoyl-L-tyrosine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 67-66-3 chloroform 

Downstream Products

• 33043-66-2 (S)-4-(4-(R)-tetrahydropyran-2-yloxy-benzyl)-oxazolidine-2,5-dione 
• 33043-65-1 (S)-4-(4-(S)-tetrahydropyran-2-yloxy-benzyl)-oxazolidine-2,5-dione 
• 34545-71-6 (S)-3-trimethylsilanyl-4-(4-trimethylsilanyloxy-benzyl)-oxazolidine-2,5-dione 
• 23224-65-9 L-Tyr(OAc) NCA 

Relevant articles and documents

-

-

METHOD FOR PREPARATION OF N-CARBOXYANHYDRIDES

The invention discloses a method for the preparation off N-carboxyanhydrides (NCAs) by reaction of amino acids with phosgene.(II)

Enzyme responsive supramolecular hydrogels assembled from nonionic peptide amphiphiles

Smart peptide hydrogels are of great interest for their great potential applications. Here, we report a facile approach to prepare a class of enzyme-responsive hydrogels in a scalable manner. These hydrogels self-assemble from a family of nonionic peptide amphiphiles (PAs) synthesized by sequential ring-opening polymerization (ROP) of γ-benzyl-L-glutamate N-carboxyanhydride (BLG-NCA) and L-tyrosine N-carboxyanhydride (Tyr-NCA), followed by subsequent aminolysis. These PA samples can readily form a clear hydrogel with a critical gelation concentration as low as 0.5 wt%. The incorporation of tyrosine residues offers hydrophobicity, hydrogen-bonding interaction and enzyme-responsive properties. The hydrogel-to-nanogel transition is observed under physiological conditions in the presence of horseradish peroxidase (HRP) and hydrogen peroxide (H2O2). The obtained PA hydrogels are ideal candidates for the new generation of smart scaffolds.

Combined atom-transfer radical polymerization and ring-opening polymerization to design polymer-polypeptide copolymer conjugates toward self-aggregated hybrid micro/nanospheres for dye encapsulation

A designed orthogonal dual initiator is employed to construct poly(methyl methacrylate)-block-polytyrosine copolymer conjugates via the combination of atom-transfer radical polymerization of methyl methacrylate, "click" chemistry and ring-opening polymerization of tyrosine-α-amino acid N-carboxyanhydride monomer. The polymer-polypeptide conjugate undergoes self-aggregation in dimethylformamide to produce hybrid micro/nanospheres owing to the formation of composite micelle as evidenced from field emission scanning electron microscopy and dynamic light scattering study. A simple solution-based approach is described to encapsulate an organic dye (Rhodamine-6G) into the aggregated hybrid micro/nanospheres.