125507-17-7

Basic information

• Product Name: 2-L-alanylmethotrexate
• Synonyms: 2-L-alanylmethotrexate
• CAS NO: 125507-17-7
• Molecular Weight: 525.524
• Mol File: 125507-17-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-L-alanylmethotrexate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-L-alanylmethotrexate(125507-17-7)
• EPA Substance Registry System: 2-L-alanylmethotrexate(125507-17-7)

Safety Data

• Hazardous Substances Data: 125507-17-7(Hazardous Substances Data)

Upstream product

• 125507-11-1 (S)-2-(4-{[4-Amino-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-pteridin-6-ylmethyl]-methyl-amino}-benzoylamino)-pentanedioic acid di-tert-butyl ester 
• 125507-15-5 (S)-2-(4-{[2,4-Bis-((S)-2-tert-butoxycarbonylamino-propionylamino)-pteridin-6-ylmethyl]-methyl-amino}-benzoylamino)-pentanedioic acid di-tert-butyl ester 
• 86669-33-2 methotrexate di-t-butyl ester 
• 16874-06-9 di-tert-butyl L-glutamate 

Downstream Products

• 59-05-2 N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid 

Relevant articles and documents

N-(L-α-aminoacyl) derivatives of methotrexate

Methotrexate di-t-butyl ester 3 was coupled with N-t-butyloxycarbonyl-L-leucine by the p-nitrophenyl ester and carbodiimide methods to give the di-t-butyl esters 5a - 7a of 2-, 4-, and 2,4-di(N-t-butyloxycarbonyl-L-leucyl)methotrexate. The corresponding L-alanyl analogues 5b - 7b were also synthesised by the latter method. The positions of the acyl groups uere determined from 13C-nmr and uv data. Upon deprotection with trifluoroacetic acid, the 2-acyl products 5a and 5b yielded 2-L-leucyl- and 2-L-alanylmethotrexate 4a and 4b, but the 4-acyl analogues 6a and 6b gave decomposition products. The enzymic cleavage of the 2-(L-α-aminoacyl) pro-drug derivatives 4a and 4b by porcine microsomal leucine aminopeptidase was followed by high-pressure liquid-chromatography (HPLC).