(6S)-Tetrahydrofolic Acid

• CAT Number: R056803
• CAS Number: 71963-69-4
• Molecular Formula: C19H23N7O6
• Molecular Weight: 445.436
• Purity: ≥95%
• Synonyms: (S)-N-[4-[[(2-Amino-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic Acid
• Target: Endogenous Metabolite
• Storage: -20°C
• IUPAC Name: (2S)-2-[[4-[[(6S)-2-amino-4-oxo-4a,5,6,7-tetrahydro-1H-pteridin-6-yl]methylamino]benzoyl]amino]pentanedioic acid
• InChI: InChI=1S/C19H23N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,11-12,14,21,23H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)/t11-,12-,14?/m0/s1
• InChIKey: GTHBYNYDVOUIBB-VHBIQUBJSA-N
• SMILES: C1C(NC2C(=N1)NC(=NC2=O)N)CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O

(6S)-Tetrahydrofolic acid is a diastereomer of tetrahydrofolic acid (Item No. 20526), a reduced form of folic acid that serves as a cofactor in methyltransferase reactions and is the major one-carbon carrier in one carbon metabolism. (6S)-Tetrahydrofolic acid is 1,000-fold more active than the (6R) form at promoting the binding of fluorodeoxyuridylate to thymidylate synthase and 600-fold more active as a growth factor of P. cerevisiae. (6S)-Tetrahydrofolic acid also has a low affinity and high dissociation rate for folate-binding protein.