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
• Article Data: 4

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

MNI-caged-L-glutamate, is a new caged neuroactive amino acid, that use 4-methoxy-7-nitroindolinyl- (MNI) group to make caged ligands specific for glutamate receptor sub-types. MNI-caged-L-glutamate, rapidly release glutamate when photolysed.

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 
• 444189-55-3 4-methoxy-7-nitroindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester 
• 7555-94-4 4-methoxy-2,3-dihydro-1H-indole 
• 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 

Downstream Products

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

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.

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.