132487-03-7

Basic information

• Product Name: (6R)-5,10-dideaza-5,6,7,8-tetrahydropteroyl-L-glutamate-(γ-L-glutamate)2
• CAS NO: 132487-03-7
• Molecular Weight: 701.69
• Mol File: 132487-03-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (6R)-5,10-dideaza-5,6,7,8-tetrahydropteroyl-L-glutamate-(γ-L-glutamate)2(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-5,10-dideaza-5,6,7,8-tetrahydropteroyl-L-glutamate-(γ-L-glutamate)2(132487-03-7)
• EPA Substance Registry System: (6R)-5,10-dideaza-5,6,7,8-tetrahydropteroyl-L-glutamate-(γ-L-glutamate)2(132487-03-7)

Safety Data

• Hazardous Substances Data: 132487-03-7(Hazardous Substances Data)

Upstream product

• 136210-14-5 (R)-(-)-4-<2-(2-Amino-1,4,5,6,7,8-hexahydro-4-oxopyrido<2,3-d>pyrimidin-6-yl)ethyl>benzonic acid 
• 71989-18-9 Fmoc-Glu(OtBu)-OH 
• 84793-07-7 Fmoc-Glu-OtBu 
• 7446-63-1 L-glutamyl-(γ-L-glutamate)2 

Relevant articles and documents

Synthesis of (6R)- And (6S)-5,10-dideazatetrahydrofolate oligo-γ-glutamates: Kinetics of multiple glutamate ligations catalyzed by folylpoly-γ-glutamate synthetase

Folylpoly-γ-glutamate synthetase (FPGS, EC 6.3.2.17) catalyzes the ATP-dependent ligation of glutamic acid to reduced folates including (6S)-5,6,7,8-tetrahydrofolate (H4PteGlu), as well as to anticancer drugs such as 5,10-dideaza-5,6,7,8-tetrahydrofolate ((6R)-DDAH 4PteGlu1, (6R)-DDATHF, Lometrexol(tm)). Synthesis of unlabeled mono- and polyglutamates, DDAH4PteGlu n (6R, n = 1-6; 6S, n = 1-2), as well as (6R)-DDAH 4Pte[14C]Glu1, was effected from (6R)- or (6S)-5,10-dideazatetrahydropteroyl azide and glutamic acid, H-Glu-γ- Glun-y-Glu-OH (n = 0-4), or [14C]glutamic acid, respectively. These compounds were evaluated as FPGS substrates to determine steady-state kinetic constants. Michaelis-Menten kinetics were observed for (6-R)-DDAH4PteGlu1, the isomer corresponding to H 4PteGlu, whereas marked substrate inhibition was observed for (6S)-DDAH4PteGlun (n = 1-2) and (6R)-DDAH 4PteGlun (n = 2-5), but not (6.R)-DDAH 4PteGlu6. Multiple ligation of glutamate renders a quantitative analysis of these data difficult. However, approximate values of KM = 0.65-1.6 μM and K1, = 144-417 μM for DDAH 4PteGln were obtained using a simple kinetic model. The Royal Society of Chemistry 2005.