238418-69-4

Basic information

• Product Name: D-Glutamine, 4-fluoro-, (4R)-rel- (9CI)
• Synonyms: D-Glutamine, 4-fluoro-, (4R)-rel- (9CI);PGEYFCBAWGQSGT-PWNYCUMCSA-N
• CAS NO: 238418-69-4
• Molecular Formula: C5H9FN2O3
• Molecular Weight: 164.1349632
• Product Categories: GLYCINESCAFFOLD
• Mol File: 238418-69-4.mol

Chemical Properties

• Boiling Point: 462.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.410±0.06 g/cm3(Predicted)
• PKA: 2.06±0.10(Predicted)
• CAS DataBase Reference: D-Glutamine, 4-fluoro-, (4R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glutamine, 4-fluoro-, (4R)-rel- (9CI)(238418-69-4)
• EPA Substance Registry System: D-Glutamine, 4-fluoro-, (4R)-rel- (9CI)(238418-69-4)

Safety Data

• Hazardous Substances Data: 238418-69-4(Hazardous Substances Data)

Usage

Uses

Used in Medical Imaging:
D-Glutamine, 4-fluoro-, (4R)-rel(9CI) is used as a tracer in the field of medical imaging, specifically for positron emission tomography (PET). The application reason is to aid in the understanding of the phenomenon of cancer cells' strong requirement for glutamine, which can provide valuable insights into cancer biology and potentially lead to the development of targeted therapies.

Upstream product

• 2358-03-4 erythro-4-fluoroglutamic acid 5-methyl ester 
• 26432-31-5 4-fluoroglutamic acid 
• 1262523-74-9 (2S,4S)-tert-butyl-2-(tert-butoxycarbonylamino)-4-fluoro-5-oxo-5-(2,4,6-trimethoxybenzylamino)pentanoate 

Relevant articles and documents

Synthesis of optically pure 4-fluoro-glutamines as potential metabolic imaging agents for tumors

A versatile synthetic route to prepare all four stereoisomeric 4-fluoro-glutamines was developed by exploiting a Passerini three-component reaction. The skeleton of 4-substituted glutamine derivatives was efficiently constructed. Subsequent four-step reactions, highlighted by a "neutralized" TASF fluorination, provided the desired products with high yields and excellent optical purity. The optically pure fluorine-18 labeled 4-fluoroglutamines were also successfully prepared using either a 18-crown-6/KHCO3 or K[222]/K2CO3 catalysis system. Preliminary cell uptake and inhibition studies using the 9L tumor cells ana SF188BC1-XL tumor cells (a glutamine addicted tumor derived from glioblastoma) provided strong evidence for their potential application in conjunction with positron emission tomography (PET) for in vivo imaging of tumors, which use glutamine as an alternative energy source.

SINGLE DIASTEREOMERS OF 4-FLUOROGLUTAMINE AND METHODS FO THEIR PREPARATION AND USE

The present invention is directed single diasteromers of 4-fluoroglutamine having a diastereomeric excess of at least 80%. Methods of preparing the single diastereomers are also described, as well as methods of using the single diastereomers of radiolabeled 4-fluoroglutamine as imaging agent is also described.

Chemistry of 4-fluoroglutamic acid. Part 3. Preparation of the diastereomers of 4-fluoroglutamine and 4-fluoroisoglutamine. An enzymatic access to the antipodes of 4-amino-2-fluorobutyric acid

The pure diastereomers of 4-fluoroglutamine and 4-fluoroisoglutamine were prepared from the corresponding 4-fluoroglutamic acids. Glutamic decarboxylase treatment of the acids led to chiral 2-fluoroGABA.