Keto-pantoyllactone

• CAT Number: I014423
• CAS Number: 13031-04-4
• Molecular Formula: C6H8O3
• Molecular Weight: 128.13
• Purity: ≥95%
• Synonyms: Keto-pantoyllactone; Keto pantoyllactone; Ketopantoyllactone;;2,3-Furandione, dihydro-4,4-dimethyl-
• Solubility: Soluble in DMSO
• Storage: 2-8°C
• IUPAC Name: 4,4-dimethyloxolane-2,3-dione
• InChI: InChI=1S/C6H8O3/c1-6(2)3-9-5(8)4(6)7/h3H2,1-2H3
• InChIKey: HRTOQFBQOFIFEE-UHFFFAOYSA-N
• SMILES: CC1(COC(=O)C1=O)C

Keto-pantoyllactone（Cat No.:I014423）, also known as a 2-ketopantoic acid lactone, is an organic compound belonging to the lactone group. It is derived from pantothenic acid, an essential nutrient involved in various biological processes. Keto-pantoyllactone is primarily used in scientific research, particularly in the study of enzymatic reactions and coenzyme A (CoA) metabolism. Its chemical structure and properties make it suitable for spectrophotometric assays, where it can be measured by its ability to catalyze the oxidation of nicotinamide adenine dinucleotide phosphate (NADPH).

Reference

1: Qin HM, Yamamura A, Miyakawa T, Kataoka M, Nagai T, Kitamura N, Urano N, Maruoka S, Ohtsuka J, Nagata K, Shimizu S, Tanokura M. Structure of conjugated polyketone reductase from Candida parapsilosis IFO 0708 reveals conformational changes for substrate recognition upon NADPH binding. Appl Microbiol Biotechnol. 2014 Jan;98(1):243-9. doi: 10.1007/s00253-013-5073-9. Epub 2013 Jul 5. PubMed PMID: 23828603. 2: Lanzilotta RP, Bradley DG, McDonald KM. Microbial reduction of ketopantoyl lactone to pantoyl lactone. Appl Microbiol. 1974 Jan;27(1):130-4. PubMed PMID: 4589122; PubMed Central PMCID: PMC379980. 3: King HL Jr, Dyar RE, Wilken DR. Ketopantoyl lactone and ketopantoic acid reductases. Characterization of the reactions and purification of two forms of ketopantoyl lactone reductase. J Biol Chem. 1974 Aug 10;249(15):4689-95. PubMed PMID: 4603075. 4: Hata H, Shimizu S, Hattori S, Yamada H. Ketopantoyl lactone reductase is a conjugated polyketone reductase. FEMS Microbiol Lett. 1989 Mar;49(1):87-90. PubMed PMID: 2656398. 5: Shimizu S, Hattori S, Hata H, Yamada H. One-Step Microbial Conversion of a Racemic Mixture of Pantoyl Lactone to Optically Active d-(-)-Pantoyl Lactone. Appl Environ Microbiol. 1987 Mar;53(3):519-22. PubMed PMID: 16347301; PubMed Central PMCID: PMC203699. 6: Si D, Urano N, Shimizu S, Kataoka M. LplR, a repressor belonging to the TetR family, regulates expression of the L-pantoyl lactone dehydrogenase gene in Rhodococcus erythropolis. Appl Environ Microbiol. 2012 Nov;78(22):7923-30. doi: 10.1128/AEM.01583-12. Epub 2012 Aug 31. PubMed PMID: 22941082; PubMed Central PMCID: PMC3485960. 7: Hata H, Shimizu S, Hattori S, Yamada H. Ketopantoyl-lactone reductase from Candida parapsilosis: purification and characterization as a conjugated polyketone reductase. Biochim Biophys Acta. 1989 Feb 24;990(2):175-81. PubMed PMID: 2644973. 8: Wilken DR, King HL Jr, Dyar RE. Ketopantoic acid and ketopantoyl lactone reductases. Stereospecificity of transfer of hydrogen from reduced nicotinamide adenine dinucleotide phosphate. J Biol Chem. 1975 Mar 25;250(6):2311-4. PubMed PMID: 234966. 9: Wilken DR, Dyar RE. Stereospecificity of pantoyl lactone formed by yeast cells and purified yeast ketopantoyl lactone reductases. Arch Biochem Biophys. 1978 Aug;189(2):251-5. PubMed PMID: 360991. 10: Shimizu S, Hattori S, Hata H, Yamada H. A novel fungal enzyme, NADPH-dependent carbonyl reductase, showing high specificity to conjugated polyketones. Purification and characterization. Eur J Biochem. 1988 May 16;174(1):37-44. PubMed PMID: 3286260. 11: Si D, Urano N, Nozaki S, Honda K, Shimizu S, Kataoka M. L-pantoyl lactone dehydrogenase from Rhodococcus erythropolis: genetic analyses and application to the stereospecific oxidation of L-pantoyl lactone. Appl Microbiol Biotechnol. 2012 Jul;95(2):431-40. doi: 10.1007/s00253-012-3970-y. Epub 2012 Mar 8. PubMed PMID: 22398860. 12: Qin HM, Yamamura A, Miyakawa T, Kataoka M, Maruoka S, Ohtsuka J, Nagata K, Shimizu S, Tanokura M. Crystal structure of conjugated polyketone reductase (CPR-C1) from Candida parapsilosis IFO 0708 complexed with NADPH. Proteins. 2013 Nov;81(11):2059-63. doi: 10.1002/prot.24363. Epub 2013 Aug 23. PubMed PMID: 23852710. 13: Kataoka M, Delacruz-Hidalgo AR, Akond MA, Sakuradani E, Kita K, Shimizu S. Gene cloning and overexpression of two conjugated polyketone reductases, novel aldo-keto reductase family enzymes, of Candida parapsilosis. Appl Microbiol Biotechnol. 2004 Apr;64(3):359-66. Epub 2003 Oct 31. PubMed PMID: 14593510. 14: Kataoka M, Shimizu S, Yamada H. Purification and characterization of a novel FMN-dependent enzyme. Membrane-bound L-(+)-pantoyl lactone dehydrogenase from Nocardia asteroides. Eur J Biochem. 1992 Mar 1;204(2):799-806. PubMed PMID: 1541293. 15: Yamamura A, Maruoka S, Ohtsuka J, Miyakawa T, Nagata K, Kataoka M, Kitamura N, Shimizu S, Tanokura M. Expression, purification, crystallization and preliminary X-ray analysis of conjugated polyketone reductase C2 (CPR-C2) from Candida parapsilosis IFO 0708. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2009 Nov 1;65(Pt 11):1145-8. doi: 10.1107/S1744309109038238. Epub 2009 Oct 30. PubMed PMID: 19923737; PubMed Central PMCID: PMC2777045. 16: Shimizu S, Kataoka M, Chung MC, Yamada H. Ketopantoic acid reductase of Pseudomonas maltophilia 845. Purification, characterization, and role in pantothenate biosynthesis. J Biol Chem. 1988 Aug 25;263(24):12077-84. PubMed PMID: 3042788. 17: Salinas Y, Oliart RM, Ramírez-Lepe M, Navarro-Ocaña A, Valerio-Alfaro G. Synthesis of chiral alpha-hydroxy amides by two sequential enzymatic catalyzed reactions. Appl Microbiol Biotechnol. 2007 May;75(2):297-302. Epub 2007 Feb 7. PubMed PMID: 17285287. 18: Nakamura K, Kondo S, Ohno A. Effect of cyclodextrin on improvement of enantioselectivity in the reduction of ketopantolactone with baker’s yeast. Bioorg Med Chem. 1994 Jun;2(6):433-7. PubMed PMID: 8000865. 19: Bonalumi N, Bürgi T, Baiker A. Interaction between ketopantolactone and chirally modified Pt investigated by attenuated total reflection IR concentration modulation spectroscopy. J Am Chem Soc. 2003 Nov 5;125(44):13342-3. PubMed PMID: 14583014. 20: Zhao M, Gao L, Zhang L, Bai Y, Chen L, Yu M, Cheng F, Sun J, Wang Z, Ying X. Asymmetric reduction of ketopantolactone using a strictly (R)-stereoselective carbonyl reductase through efficient NADPH regeneration and the substrate constant-feeding strategy. Biotechnol Lett. 2017 Nov;39(11):1741-1746. doi: 10.1007/s10529-017-2415-1. Epub 2017 Aug 21. PubMed PMID: 28828561.