MNI-caged-L-glutamate

Base Information

• Chemical Name: MNI-caged-L-glutamate
• CAS No.: 295325-62-1
• Molecular Formula: C14H17 N3 O6
• Molecular Weight: 323.305
• DSSTox Substance ID: DTXSID80424987
• Nikkaji Number: J2.997.254K
• Wikidata: Q82237736
• ChEMBL ID: CHEMBL1413097
• Mol file: 295325-62-1.mol

Synonyms:MNI-caged-L-glutamate;295325-62-1;(S)-2-Amino-5-(4-methoxy-7-nitroindolin-1-yl)-5-oxopentanoic acid;4-Methoxy-7-nitroindolinyl-L-glutamate;4-Methoxy-7-nitroindolinyl-caged-L-glutamate;(S)-alpha-amino-2,3-dihydro-4-methoxy-7-nitro-D-oxo-1H-indole-1-pentanoic acid;MNI glutamate;(2S)-2-amino-5-(4-methoxy-7-nitro-2,3-dihydroindol-1-yl)-5-oxopentanoic acid;NCGC00025183-01;Tocris-1490;SCHEMBL3896563;CHEMBL1413097;DTXSID80424987;HB0423;AKOS024456634;AKOS040745244;BM162483;PD071035;SR-01000597600;J-017553;SR-01000597600-1;(S)-2-Amino-5-(4-methoxy-7-nitroindolin-1-yl)-5-oxopentanoicacid;(2S)-2-Amino-5-(4-methoxy-7-nitro-2,3-dihydro-1H-indole-1-yl)-5-oxopentanoic acid;(S)-?-Amino-2,3-dihydro-4-methoxy-7-nitro-?-oxo-1H-indole-1-pentanoic acid;(S)-alpha-Amino-2,3-dihydro-4-methoxy-7-nitro-delta-oxo-1H-indole-1-pentanoic acid

Chemical Property of MNI-caged-L-glutamate

Chemical Property:

• PSA: 138.68000
• LogP: 1.97310
• Storage Temp.: Store at -20°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 323.11173527
• Heavy Atom Count: 23
• Complexity: 480

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

MNI-caged-L-glutamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2CCN(C2=C(C=C1)[N+](=O)[O-])C(=O)CCC(C(=O)O)N
• Isomeric SMILES: COC1=C2CCN(C2=C(C=C1)[N+](=O)[O-])C(=O)CC[C@@H](C(=O)O)N
• 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.

Technology Process of MNI-caged-L-glutamate

There total 8 articles about MNI-caged-L-glutamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

4-methoxy-7-nitroindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester (444189-55-3) → 1-[(S)-(4-amino-4-carboxybutanoyl)]-4-methoxy-7-nitroindoline (295325-62-1)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 1h;

DOI:10.1081/SCC-120004148

Reference yield:

4-methoxyindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester (314760-11-7) → 1-[(S)-(4-amino-4-carboxybutanoyl)]-4-methoxy-7-nitroindoline (295325-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / montmorillonite K₁₀/Cu(NO₃)2; acetic anhydride / CCl₄ / 20 °C

2: 87 percent / TFA / 1 h / 20 °C

With Montmorillonite K₁₀; acetic anhydride; copper(II) nitrate; trifluoroacetic acid; In tetrachloromethane;

DOI:10.1081/SCC-120004148

Reference yield:

4-methoxy-2,3-dihydro-1H-indole (7555-94-4) → 1-[(S)-(4-amino-4-carboxybutanoyl)]-4-methoxy-7-nitroindoline (295325-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide; DMAP / acetonitrile / 16 h / 20 °C

2: NaNO₃; trifluoroacetic acid / 0.67 h / -15 °C

With dmap; sodium nitrate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In acetonitrile; 1: Acylation / 2: Nitration;

DOI:10.1016/S0040-4020(00)00745-6

upstream raw materials:

4-methoxyindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester

4-methoxy-7-nitroindolinyl N-α-(tert-butoxycarbonyl)-L-glutamic acid α-tert-butyl ester

4-methoxy-2,3-dihydro-1H-indole

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

Downstream raw materials:

L-glutamate

L-glutamic acid

4-methoxy-7-nitrosoindole

Refernces

• 1、 Papageorgiou, George,Corrie, John E. T.. "Regioselective nitration of 1-acyl-4-methoxyindolines leads to efficient synthesis of a photolabile L-glutamate precursor". . p. 1571 - 1577. Retrieved 2002.
• 2、 Papageorgiou, George,Corrie, John E.T. "Effects of aromatic substituents on the photocleavage of 1-acyl-7-nitroindolines". . p. 8197 - 8205. Retrieved 2007/10/03.