2650-64-8

Basic information

• Product Name: N-Carbobenzyloxy-L-glutamine
• Synonyms: CBZ-L-GLUTAMINE;CBZ-L-GLN;CBZ-L-GLN-OH;CBZ-GLN-OH;BENZYLOXYCARBONYL-L-GLUTAMINE;CARBOBENZYLOXY-L-GLUTAMINE;N-CBZ-L-GLUTAMINE;N(ɑ)-Benzyloxycarbonyl-L-glutamine, 99%
• CAS NO: 2650-64-8
• Molecular Formula: C₁₃H₁₆N₂O₅
• Molecular Weight: 280.28
• EINECS: 220-173-8
• Product Categories: PROTECTED AMINO ACID & PEPTIDES;Glutamine [Gln, Q];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Chiral Compounds;Z-Amino acid series;Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 2650-64-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 134-138 °C(lit.)
• Boiling Point: 423°C (rough estimate)
• Flash Point: 319.2 °C
• Appearance: white to off-white powder
• Density: 1.2419 (rough estimate)
• Vapor Pressure: 1.9E-15mmHg at 25°C
• Refractive Index: 1.6450 (estimate)
• Storage Temp.: -20°C
• Solubility: DMSO, Ethanol, Methanol
• PKA: 3.82±0.10(Predicted)
• BRN: 2061271
• CAS DataBase Reference: N-Carbobenzyloxy-L-glutamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Carbobenzyloxy-L-glutamine(2650-64-8)
• EPA Substance Registry System: N-Carbobenzyloxy-L-glutamine(2650-64-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2650-64-8(Hazardous Substances Data)

Usage

Description

N-Carbobenzyloxy-L-glutamine, also known as Z-Gln-OH or Carbobenzyloxy-glutamine, is a synthetic derivative of the naturally occurring amino acid L-glutamine. It is characterized by the presence of a carbobenzyloxy (Cbz) protecting group, which is commonly used in peptide synthesis to prevent unwanted side reactions. N-Carbobenzyloxy-L-glutamine is a white to off-white powder and has various applications in the pharmaceutical and chemical industries.

Uses

1. Used in Pharmaceutical Industry:
N-Carbobenzyloxy-L-glutamine is used as an anti-ulcer agent for the treatment of gastrointestinal ulcers. It helps in reducing the severity of ulcers and promoting the healing process.
2. Used in Agricultural Industry:
N-Carbobenzyloxy-L-glutamine is used as an inhibitor for Acetohydroxy Acid Synthase (AHAS), an important enzyme involved in the biosynthesis of branched-chain amino acids in plants. By inhibiting this enzyme, the compound can affect the herbicidal properties of certain environmental herbicides, making them more selective and less harmful to non-target plants.
3. Used in HIV Treatment:
N-Carbobenzyloxy-L-glutamine is used in the synthesis of neomycin B, an important HIV antiviral agent. It plays a crucial role in the development of drugs that can help combat the human immunodeficiency virus (HIV).
4. Used in Chemical Synthesis:
N-Carbobenzyloxy-L-glutamine is also used as a protected amino acid in the synthesis of various peptides and other bioactive compounds. The carbobenzyloxy group can be selectively removed under mild conditions, allowing for the controlled assembly of complex peptide structures.

InChI:InChI=1/C13H16N2O5/c14-11(16)7-6-10(12(17)18)15-13(19)20-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H2,14,16)(H,15,19)(H,17,18)/p-1/t10-/m0/s1

Upstream product

• 4510-09-2 N-benzyloxycarbonyl-L-glutamic acid-5-hydrazide 
• 35726-62-6 (S)-2-(benzyloxycarbonylamino)-5-ethoxy-5-oxopentanoic acid 
• 56-85-9 L-glutamine 
• 501-53-1 benzyl chloroformate 
• 4124-76-9 N-(benzyloxycarbonyl)-L-glutamic acid anhydride 
• 3077-51-8 γ-methyl L-glutamate hydrochloride 
• 38596-35-9 dicyclohexylamine salt of N-benzyloxycarbonyl-(L)-pyroglutamic acid 
• 75819-24-8 3-benzyloxycarbonyl-2-oxazolone 
• 250296-57-2 N-Benzyloxycarbonyl-N-trifluoromethylsulfonyl-4-trifluoromethylanilide 
• 100-51-6 benzyl alcohol 

Downstream Products

• 13907-82-9 N²-benzyloxycarbonyl-L-glutamine methyl ester 
• 7763-16-8 N²-benzyloxycarbonyl-L-glutamine-(4-nitro-phenyl ester) 
• 123-91-1 1,4-dioxane 
• 2658-34-6 S-benzyl-N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-L-asparaginyl]-L-cysteine methyl ester 
• 16869-66-2 S-benzyl-N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-cysteine methyl ester 
• 122242-44-8 S-benzyl-N-[S-benzyl-N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-cysteinyl]-L-cysteine ethyl ester 
• 2731-88-6 Z-Gln-Gly-OEt 
• 122315-76-8 S-benzyl-N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-cysteine ethyl ester 
• 49761-50-4 N-(N²-benzyloxycarbonyl-L-glutaminyl)-L-alanine benzyl ester 
• 121426-62-8 N-[N²-(N²-benzyloxycarbonyl-L-glutaminyl)-glutaminyl]-L-alanine 
• 2899-14-1 Z-Gln-N₂H₂-Boc 
• 95700-16-6 benzyl 5-amino-2-(((benzyloxy)carbonyl)amino)-5-oxopentanoate 
• 57294-48-1 Z-Glu(-NH₂)-Gly-OBzl 
• 14349-35-0 Benzyloxycarbonyl-L-glutaminyl-glycin-(4-nitro-benzylester) 

Relevant articles and documents

Preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid

The invention discloses a preparation method of (S)-1 - (benzyloxycarbonyl) -5 -oxo-pyrrolidine -2 - formic acid, which mainly solves the complexity in the original process, and is long in period and high in cost. The method specifically comprises first steps of preparing L - benzyloxycarbonyl N - glutamic acid from - L - glutamic acid and a benzyloxycarbonyl donor, second steps of intramolecular condensation cyclization N - benzyloxycarbonyl - L - glutamic acid to obtain the N -benzyloxycarbonyl - L - glutamic acid crude product. The third The crude N - benzyloxycarbonyl - L - glutamic acid crude product and the organic amine base are mixed, and the organic amine salt form is prepared by the solubility of the product in a solvent, fourth (N -) - L - (benzyloxycarbonyl) S oxopyrrolidine -1 - formic acid is prepared by desalinating -5 - benzyloxycarbonyl -2 - glutamic acid. To the method, the high-purity product is prepared, and the yield and the quality are greatly improved.

Preparation method of deuterated intermediate

The present invention provides a preparation method of a deuterated intermediate. The deuterated intermediate has a structure shown by a formula I; the preparation method comprises the following steps: amino groups in a raw material A and an aldehyde grou

(S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method

The present invention relates to a (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method. According to the method, L-glutamine is used as a raw material, the alpha-amino of the L-glutamine is protected with a protection group, a decarbonylating agent is added, a Hofmann degradation reaction is performed to remove the carbonyl group attached to the remaining amino, the protection group is removed to obtain L-2,4-diaminobutyric acid, and finally the prepared L-2,4-diaminobutyric acid and trimethyl orthoacetate are subjected to a ring forming reaction to obtain the (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid. Compared to the method in the prior art, the method of the present invention has the following characteristics that the chemical synthesis route is provided, the steps of the synthesis process are simple, the raw materials are easy to obtain, the product purity is high, and the method is suitable for large-scale industrial production.