51865-82-8

Basic information

• Product Name: N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine
• Synonyms: lysine, N~2~-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-N~6~-[(phenylmethoxy)carbonyl]-
• CAS NO: 51865-82-8
• Molecular Formula: C₂₉H₃₃N₉O₅
• Molecular Weight: 587.6296
• Mol File: 51865-82-8.mol
• Article Data: 3

Chemical Properties

• Density: 1.387g/cm³
• Refractive Index: 1.685
• CAS DataBase Reference: N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine(CAS DataBase Reference)
• NIST Chemistry Reference: N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine(51865-82-8)
• EPA Substance Registry System: N~6~-[(benzyloxy)carbonyl]-N~2~-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)lysine(51865-82-8)

Safety Data

• Hazardous Substances Data: 51865-82-8(Hazardous Substances Data)

Upstream product

• 56892-71-8 4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoic O-isobutyl-carbonic anhydride 
• 7532-09-4 methotrexate sodium salt 
• 5978-22-3 N(ε)-benzoyloxycarbonyl-L-lysine tert-butyl ester hydrochloride 
• 19741-14-1 4-[(2,4-diaminopteridin-6-ylmethyl)methylamino]benzoic acid 
• 56892-79-6 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-carbobenzoxy-L-lysine methyl ester 

Downstream Products

• 82339-36-4 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-N^ε-(iodoacetyl)-L-lysine 
• 80407-56-3 N^α-(4-amino-4-deoxy-N¹⁰-methylpteroyl)-L-lysine 

Relevant articles and documents

Methotrexate analogues. 15. A methotrexate analogue designed for active-site-directed irreversible inactivation of dihydrofolate reductase

N(a)-(4-Amino-4-deoxy-N10-methylpteroyl)-N4-(iodoacetyl)-L-lysine (1) was synthesized as a potential active-site-directed irreversible inhibitor or dihydrofolate reductase (DHFR). In an ultraviolet spectrophotometric assay of dihydrofolate reduction by Lactobacillus casei DHFR, 1 and methotrexate (MTX, 4-amino-4-deoxy-N10-methylpteroyl-L-glutamic acid) had ID50 values of 4.5 and 6.2 nM. The corresponding ID50 values in a competitive radioligand binding assay against [3H]MTX were 31 and 16 nM. Thus, as reversible inhibitors of this enzyme over a short exposure time, 1 and MTX had comparable activity. On the other hand, when L. casei DHFR was incubated for up to 6 h with 0.1 or 1.0 μM 1, a progressive decrease in the ability of [3H]MTX to subsequently displace the drug was observed. When MTX itself was used at the same concentrations, the extent of displacement of [3H]MTX did not decrease with time. These results were consistent with rapid reversible binding of 1 to the enzyme, followed more slowly by covalent bond formation near the active site. The pH profile for this effect followed a curve with a sigmoidal shape. The apparent inflection point near pH 7.2 was consistent with alkylation of a histidine residue.

Folic acid antagonists. Methotrexate analogs containing spurious amino acids. Dichlorohomofolic acid

The synthesis and some biological testing results are reported for dichlorohomofolic acid (2a) and 3 methotrexate (MTX) analogs in which the L glutamic acid moiety was replaced by D glutamic acid, glutaric acid, and L lysine to give 4b, 4c, and 4d, respec