WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 597243
CAS#: 33611-85-7
Description: Pteroylpentaglutamic acid is a bioactive chemical within the folic acid family.
MedKoo Cat#: 597243
Name: Pteroylpentaglutamic acid
CAS#: 33611-85-7
Chemical Formula: C39H47N11O18
Exact Mass: 957.3101
Molecular Weight: 957.86
Elemental Analysis: C, 48.90; H, 4.95; N, 16.09; O, 30.07
This product is not in stock, which may be available by custom synthesis.
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Synonym: Pteroylpentaglutamic acid; Pte-penta-glu; NSC 372667; NSC-372667; NSC372667;
IUPAC/Chemical Name: (3S,8S,13S,18S,23S)-1-(4-(((2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl)amino)phenyl)-1,6,11,16,21-pentaoxo-2,7,12,17,22-pentaazapentacosane-3,8,13,18,23,25-hexacarboxylic acid
InChi Key: IVSPPVMFGMVDLI-LSBAASHUSA-N
InChi Code: InChI=1S/C39H47N11O18/c40-39-49-31-30(33(58)50-39)43-19(16-42-31)15-41-18-3-1-17(2-4-18)32(57)48-24(38(67)68)8-13-28(54)46-22(36(63)64)6-11-26(52)44-20(34(59)60)5-10-25(51)45-21(35(61)62)7-12-27(53)47-23(37(65)66)9-14-29(55)56/h1-4,16,20-24,41H,5-15H2,(H,44,52)(H,45,51)(H,46,54)(H,47,53)(H,48,57)(H,55,56)(H,59,60)(H,61,62)(H,63,64)(H,65,66)(H,67,68)(H3,40,42,49,50,58)/t20-,21-,22-,23-,24-/m0/s1
SMILES Code: O=C(O)CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(CC[C@@H](C(O)=O)NC(C1=CC=C(NCC2=CN=C3NC(N)=NC(C3=N2)=O)C=C1)=O)=O)=O)=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
The following data is based on the product molecular weight 957.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Choi JH, Yates Z, Martin C, Boyd L, Ng X, Skinner V, Wai R, Kim J, Woo HD, Veysey M, Lucock M. Genetic Variation in Glutamate Carboxypeptidase II and Interaction with Dietary Natural Vitamin C May Predict Risk for Adenomatous Polyp Occurrence. Asian Pac J Cancer Prev. 2015;16(10):4383-6. PubMed PMID: 26028103.
2: Smith J, Empson M, Wall C. Recurrent anaphylaxis to synthetic folic acid. Lancet. 2007 Aug 25;370(9588):652. PubMed PMID: 17720006.
3: Holm J, Hansen SI. Ligand binding characteristics of two molecular forms, one equipped with a hydrophobic glycosyl phosphatidylinositol tail, of the folate binding protein purified from human milk. Biosci Rep. 2002 Jun-Aug;22(3-4):455-63. PubMed PMID: 12516786.
4: Heston WD. Characterization and glutamyl preferring carboxypeptidase function of prostate specific membrane antigen: a novel folate hydrolase. Urology. 1997 Mar;49(3A Suppl):104-12. PubMed PMID: 9123729.
5: Pinto JT, Suffoletto BP, Berzin TM, Qiao CH, Lin S, Tong WP, May F, Mukherjee B, Heston WD. Prostate-specific membrane antigen: a novel folate hydrolase in human prostatic carcinoma cells. Clin Cancer Res. 1996 Sep;2(9):1445-51. PubMed PMID: 9816319.
6: Wagh PV, Kalman TI. A rapid colorimetric assay for gamma-glutamyl hydrolase (conjugase). Anal Biochem. 1992 Nov 15;207(1):1-5. PubMed PMID: 1362632.
7: Krungkrai J, Webster HK, Yuthavong Y. De novo and salvage biosynthesis of pteroylpentaglutamates in the human malaria parasite, Plasmodium falciparum. Mol Biochem Parasitol. 1989 Jan 1;32(1):25-37. PubMed PMID: 2643036.
8: Rowe PB, Lewis GP. Preparative electrochemical reduction of pteroylpentaglutamate. Methods Enzymol. 1986;122:319-22. PubMed PMID: 3702698.
9: Leichter J, Krumdieck CL. Effect of oral contraceptives on intestinal folate conjugase activity and folate absorption in rats. Drug Nutr Interact. 1983;2(1):1-6. PubMed PMID: 6689590.
10: Cooper BA, Peyman J. Folic acid and its pentaglutamate leak from human erythrocyte ghosts but not from liposomes. Biochim Biophys Acta. 1982 Oct 22;692(1):161-4. PubMed PMID: 7171585.
