932735-43-8

Basic information

• Product Name: Z-DL-Gln-OH
• Synonyms: 5-AMino-4-(((benzyloxy)carbonyl)aMino)-5-oxopentanoic acid
• CAS NO: 932735-43-8
• Molecular Formula: C₁₃H₁₆N₂O₅
• Molecular Weight: 280.27654
• Mol File: 932735-43-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Z-DL-Gln-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-DL-Gln-OH(932735-43-8)
• EPA Substance Registry System: Z-DL-Gln-OH(932735-43-8)

Safety Data

• Hazardous Substances Data: 932735-43-8(Hazardous Substances Data)

Usage

General Description

Z-DL-Gln-OH, also known as N-tert-Butoxycarbonyl-5-oxo-DL-proline or Z-DL-glutamine, is a chemical compound utilized in peptide synthesis and drug development. It is derived from the amino acid glutamine and is commonly used as a building block in the creation of peptide molecules. Z-DL-Gln-OH contains a t-butoxycarbonyl (Boc) protecting group, which helps to prevent unwanted reactions during the synthesis process. Z-DL-Gln-OH is often employed in the pharmaceutical industry for the production of peptide-based drugs and as a research tool for investigating the structure and function of peptides. It is important for the development of new therapeutic agents and plays a crucial role in advancing the field of medicinal chemistry.

Upstream product

• 133464-35-4 3-benzyl 4-methyl (4R)-2,2-dimethyloxazolidine-3,4-dicarboxylate 
• 133464-37-6 (4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester 
• 932735-40-5 (3S,5S)-tert-butyl 3-(3-ethoxy-3-oxo-[2-13C]propyl)-2-oxo-5-phenylmorpholine-4-carboxylate 
• 932735-39-2 (3S,5S)-tert-butyl 3-(3-ethoxy-3-oxo-2-phenylsulfonyl-[2-13C]propyl)-2-oxo-5-phenylmorpholine-4-carboxylate 
• 932735-42-7 L-N-benzyloxycarbonyl-[4-13C]glutamic acid 5-methyl ester 

Relevant articles and documents

A simple convenient synthesis of L-[4-13C] glutamine

L-[4-13C]Glutamine was synthesized from sodium [2-13C]acetate in 12 steps and 18% overall yield. A Wittig reaction of (R)-benzyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate and ethyl 2-(triphenylphosphoranylidene)[2-13C]acetate prepared from D-serine and sodium [2-13C]acetate, respectively, gave (4S)-4-(2-ethoxycarbonyl[2-13C]vinyl)-2,2-dimethyloxazolidine-3-carboxylic acid α,β-isopropylidene group, oxidation of the resulting hydroxyl group to a carboxyl group and transamidation of the ester moiety gave L-N-Cbz-[4-13C]glutamine (Cbz = benzyloxycarbonyl). Finally, removal of the Cbz group gave L-[4-13C]glutamine. L-[4-13C]Glutamine can be prepared in fewer steps and higher yield by this method compared with previously reported methods.