103321-37-5

Basic information

• Product Name: L-Glutamic acid, N-[1-oxo-4-[[1-oxo-4-[[(phenylmethoxy)carbonyl]amino]butyl]amino]butyl] -, bis(1,1-dimethylethyl) ester
• CAS NO: 103321-37-5
• Molecular Formula: C29H45N3O8
• Molecular Weight: 563.692
• Mol File: 103321-37-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Glutamic acid, N-[1-oxo-4-[[1-oxo-4-[[(phenylmethoxy)carbonyl]amino]butyl]amino]butyl] -, bis(1,1-dimethylethyl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Glutamic acid, N-[1-oxo-4-[[1-oxo-4-[[(phenylmethoxy)carbonyl]amino]butyl]amino]butyl] -, bis(1,1-dimethylethyl) ester(103321-37-5)
• EPA Substance Registry System: L-Glutamic acid, N-[1-oxo-4-[[1-oxo-4-[[(phenylmethoxy)carbonyl]amino]butyl]amino]butyl] -, bis(1,1-dimethylethyl) ester(103321-37-5)

Safety Data

• Hazardous Substances Data: 103321-37-5(Hazardous Substances Data)

Upstream product

• 90139-76-7 4-(4-Benzyloxycarbonylamino-butyrylamino)-butyric acid methyl ester 
• 5105-78-2 4-(benzyloxycarbonylamino)butyric acid 
• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 1489-76-5 4-(4-Benzyloxycarbonylamino-butyrylamino)-butyric acid 

Downstream Products

• 103321-44-4 (S)-2-[4-(4-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid di-tert-butyl ester 
• 103321-29-5 (S)-2-[4-(4-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-pentanedioic acid 

Relevant articles and documents

Methotrexate Analogues. 29. Effect of γ-Aminobutyric Acid Spacers between the Pteroyl and Glutamate Moieties on Enzyme Binding and Cell Growth Inhibition

A series of "stretched" methotrexate (MTX) analogues containing up to five 4-aminobutyryl (Gab) spacers between the 4-amino-4-deoxy-N10-methylpteroyl (MeAPA) moiety and the glutamate (Glu) side chain was prepared.Interest in these compounds stemmed from their relationship to MTX γ-polyglutamates, from which they differ only in lacking "internal" α-carboxyl groups.The ability of the MeAPA-Gabn-Glu derivatives to inhibit dihydrofolate reductase (DHFR) and thymidylate synthase (TS) in vitro and to inhibit the growth of tumor cells in culture was evaluated.The IC50 for DHFR inhibition increased progressively from 0.082 to 0.84 μM as the number of Gab spacers was varied from one to five.At the same time the introduction of Gab spacers was found to produce substantial TS inhibition (Ki 0.1-0.4 μM) similar to that reported for MTX polyglutamates.Despite the activity of the MeAPA-Gabn-Glu derivatives as combined inhibitors of TS and DHFR, there was a steep loss of cell growth inhibitory potency as the number of Gab spacers was increased.This most likely reflects low cell uptake and the fact that when n > 1 there is almost total abolition of substrate activity for folypolyglutamate synthetase, which had previously been observed with n = 1.