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

Uses

Different sources of media describe the Uses of 3415-08-5 differently. You can refer to the following data:
1. L-Tyr-NCA is used as a reactant in the synthesis of peptides. Peptides such as glutamine penefit in optimum protein utilization for post-injury conditions.
2. N-Carbonyl-L-tyrosine Anhydride is used as a reactant in the synthesis of peptides. Peptides such as glutamine penefit in optimum protein utilization for post-injury conditions.

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 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 67-66-3 chloroform 
• 90899-85-7 N-carbamoyl-L-tyrosine 

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

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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.