295325-62-1

Basic information

• Product Name: (S)-ALPHA-AMINO-2,3-DIHYDRO-4-METHOXY-7-NITRO-D-OXO-1H-INDOLE-1-PENTANOIC ACID
• Synonyms: MNI-CAGED-L-GLUTAMATE;(S)-ALPHA-AMINO-2,3-DIHYDRO-4-METHOXY-7-NITRO-D-OXO-1H-INDOLE-1-PENTANOIC ACID;(S)-α-Amino-2,3-dihydro-4-methoxy-7-nitro-δ-oxo-1H-indole-1-pentanoicacid;GXIDBZKXGUNITQ-VIFPVBQESA-N
• CAS NO: 295325-62-1
• Molecular Formula: C₁₄H₁₇N₃O₆
• Molecular Weight: 323.3
• Mol File: 295325-62-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Store at -20°C
• Solubility: Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: (S)-ALPHA-AMINO-2,3-DIHYDRO-4-METHOXY-7-NITRO-D-OXO-1H-INDOLE-1-PENTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-ALPHA-AMINO-2,3-DIHYDRO-4-METHOXY-7-NITRO-D-OXO-1H-INDOLE-1-PENTANOIC ACID(295325-62-1)
• EPA Substance Registry System: (S)-ALPHA-AMINO-2,3-DIHYDRO-4-METHOXY-7-NITRO-D-OXO-1H-INDOLE-1-PENTANOIC ACID(295325-62-1)

Safety Data

• Hazardous Substances Data: 295325-62-1(Hazardous Substances Data)

Usage

Uses

Used in Neuroscience Research:
MNI-caged-L-glutamate is used as a research tool for studying the role of glutamate receptors in various neurological processes. Its ability to rapidly release glutamate upon photolysis enables researchers to investigate the specific functions and mechanisms of different glutamate receptor subtypes in a controlled manner.
Used in Drug Development:
MNI-caged-L-glutamate can be employed in the development of new drugs targeting glutamate receptors, which are implicated in various neurological disorders such as Alzheimer's disease, Parkinson's disease, and multiple sclerosis. By understanding the specific actions of this caged neuroactive amino acid, researchers can design more effective and targeted therapies for these conditions.
Used in Neurotransmitter Release Studies:
MNI-caged-L-glutamate is used as a research tool to study the release of neurotransmitters, particularly glutamate, in response to various stimuli. This can help researchers gain insights into the underlying mechanisms of neurotransmission and develop a better understanding of how it is regulated in the brain.
Used in Optogenetics:
MNI-caged-L-glutamate can be utilized in optogenetics, a technique that combines genetics and optics to control cells in living tissue. By using this caged neuroactive amino acid, researchers can selectively control the release of glutamate in specific neurons, allowing for the investigation of their function and interactions with other cells in the nervous system.

Biological Activity

Caged glutamate that rapidly and efficiently releases glutamate when photolysed (300-380 nm excitation). Water-soluble, highly resistant to hydrolysis, stable at neutral pH, and pharmacologically inactive at neuronal glutamate receptors (up to mM concentrations). 2.5-fold more efficient at releasing L-glutamate than NI-caged L-glutamate.

Upstream product

• 314760-11-7 4-methoxyindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester 
• 24277-39-2 N-tert-butoxycarbonyl glutamic acid tert-butyl ester 
• 2380-94-1 1H-indol-4-ol 
• 4837-90-5 4-methoxy-1H-indole 
• 7555-94-4 4-methoxy-2,3-dihydro-1H-indole 
• 444189-55-3 4-methoxy-7-nitroindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester 

Downstream Products

• 56-86-0 L-glutamic acid 
• 314760-17-3 4-methoxy-7-nitrosoindole 
• 154679-07-9 L-glutamate 

Relevant articles and documents

Efficient preparation of photolabile agent mni-glu by regioselective nitration of 4-methoxyindoline derivative

The present work investigates the nitration of 4-methoxy indoline derivative with different reagents and optimized conditions. We now report a simple methodology for nitration employing claycop in the presence of amine, which offers significant improvement with regard to the yield and regioselectivity, and a much more favorable isomeric ratio of products was obtained under mild conditions. Therefore, a useful method for preparation of a photolabile L-glutamate derivative was concurrently established.

Regioselective nitration of 1-acyl-4-methoxyindolines leads to efficient synthesis of a photolabile L-glutamate precursor

Different nitrating reagents give different ratios of 5- and 7-nitro isomers of the title indolines. The best ratio of the 7-nitro isomer was obtained with claycop-acetic anhydride, and these conditions were particularly useful for preparation of a photolabile L-glutamate derivative.

An Fmoc-compatible method for synthesis of peptides containing photocaged aspartic acid or glutamic acid

A new method compatible with 9-fluorenylmethoxycarbonyl (Fmoc) solid phase peptide synthesis (SPPS) was developed to synthesize photocaged peptides carrying the photosensitive 4-methoxy-7-nitroindoline (MNI) group on the side chain of aspartic acid (Asp) and glutamic acid (Glu). The caged building blocks, Fmoc-Asp(MNI)-OH and Fmoc-Glu(MNI)-OH, could be readily synthesized on multi-gram scale. An important advantage of the new method is that the MNI group prevents the formation of aminosuccinyl side products and pyrrolidones during Fmoc SPPS and has rapid photolysis kinetics. Thus our method provides a useful approach for photocaging of peptides and proteins at side chain carboxylic groups.

Effects of aromatic substituents on the photocleavage of 1-acyl-7-nitroindolines

Photolysis of 1-acyl-7-nitroindolines in aqueous solution gives a carboxylic acid and a 7-nitrosoindole. These compounds are useful as photolabile precursors of carboxylic acids, particularly neuroactive amino acids. The effect of electron-donating substituents at the 4-position has been explored for its effect on photolysis efficiency. 4-Methoxy substitution improved the photolysis efficiency >2-fold but the 4-dimethylamino analogue was essentially inert. A 5-alkyl substituent, that blocks unwanted nitration at this position, reduced the beneficial effect of the 4-methoxy group. (C) 2000 Elsevier Science Ltd.