79648-88-7

Basic information

• Product Name: α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate
• Synonyms: α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate
• CAS NO: 79648-88-7
• Molecular Weight: 524.58
• Mol File: 79648-88-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate(CAS DataBase Reference)
• NIST Chemistry Reference: α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate(79648-88-7)
• EPA Substance Registry System: α-tert-butyl γ-methyl N'-<4--N-methylamino>benzoyl>-L-glutamate(79648-88-7)

Safety Data

• Hazardous Substances Data: 79648-88-7(Hazardous Substances Data)

Upstream product

• 84793-07-7 Fmoc-Glu-OtBu 
• 19741-14-1 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid 
• 34582-33-7 α-tert-butyl-γ-methyl L-Glu diester hydrochloride 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 10541-83-0 N-methyl-p-aminobenzoic acid 
• 945-24-4 2,4-diamino-6-(hydroxymethyl)pteridine 
• 367275-86-3 1,1-dimethylethyl 5-methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamate 
• 2528-30-5 4-<<(benzyloxy)carbonyl>methylamino>benzoic acid 
• 79640-72-5 L-glutamic acid 1-tert-butyl ester 5-methyl ester 
• 59368-16-0 6-bromomethyl-pteridine-2,4-diamine 
• 472960-79-5 2-(4-methylamino-benzoylamino)-pentanedioic acid 1-tert-butyl ester 5-methyl ester 

Downstream Products

• 940952-00-1 C₃₀H₄₀N₈O₇ 
• 121788-84-9 (S)-2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-4-[2,2,2-trifluoro-eth-(E)-ylidene-hydrazinocarbonyl]-butyric acid 
• 121788-83-8 (S)-4-Azidocarbonyl-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyric acid 
• 79640-75-8 N'-<4--N-methylamino>benzoyl>-L-glutamic acid γ-hydrazide 
• 181040-33-5 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide 
• 181040-49-3 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1-hydroxymethyl-2-[(1-oxohexadecyl)oxy]-1-[(1-oxohexadecyl)oxymethyl]ethyl]glycinamide 
• 511544-99-3 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[1,1-bis(hydroxymethyl)-2-[(1-oxohexadecyl)oxy]ethyl]glycinamide 
• 181040-47-1 N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide 

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In order to increase the retention of drug activity, regiospecific coupling has been used to synthesize conjugates of methotrexate (MTX, 1) with normal rabbit IgG (NRG) and a mouse anti-human renal cancer monoclonal IgG (Dal K-20). MTX γ-methyl ester (4) was produced either by selective esterification of MTX or by coupling of 4-amino-4-deoxy-N10-methylpteroic acid (2) with suitable glutamic acid derivatives. The MTX γ-methyl ester (4) was then converted to the corresponding hydrazide 6. An amide-linked conjugate was formed when the MTX γ-hydrazide (6) was converted to reactive acylating species 7 by using tert-butyl nitrite or trifluoroacetaldehyde, which were reacted with nucleophilic centers, presumably ε-amino groups, in native IgG. A hydrazone-linked conjugate was formed when MTX γ-hydrazide (6) was reacted directly with IgG that had first been oxidized with periodate to form polyaldehyde IgG. The regiospecifically synthesized conjugates were somewhat more effective inhibitors in vitro of dihydrofolate reductase and of colony formation by human renal cancer (Caki-1) cells than were control nonregiospecific conjugates.