599-04-2Relevant articles and documents
R(-)PANTOYLLACTONE-β-D-GLUCOPYRANOSIDE: CHARACTERIZATION OF A METABOLITE FROM RICE SEEDLINGS
Menegus, Faustino,Cattaruzza, Liliana,Ragg, Enzio,Scaglioni, Leonardo
, p. 1617 - 1622 (1995)
A new derivative of pantoic acid, R(-)pantoyllactone-β-D-glucopyranoside, has been isolated from rice seedlings and its structure determined. β-Glucosidase hydrolysed it to D-glucose and R(-)pantoyllactone.Alkaline hydrolysis converted it to the salt of 2-R(-)pantoic acid β-D-glucopyranoside.It accumulated in rice shoots but not in roots. - Keywords: Oryza sativa; Gramineae; rice seedling; pantoyllactone glucoside; pantoic acid glucoside; new metabolite; NMR signal assignment; shoot to root distribution.
Copper-Mediated Synthesis of N-Acyl Vinylogous Carbamic Acids and Derivatives: Synthesis of the Antibiotic CJ-15,801
Han, Chong,Shen, Ruichao,Su, Shun,Porco Jr., John A.
, p. 27 - 30 (2004)
(Equation presented) Copper(I)-mediated C-N bond formation has been employed to prepare both N-acyl vinylogous carbamic acids and ureas. The novel N-acyl vinylogous carbamic acid antibiotic, CJ-15,801, was synthesized using this methodology.
Synthesis of (R)-pantoyl lactone by reduction of ketopantoate with formate and Proteus species
Eck,Simon
, p. 1419 - 1422 (1994)
(R)-Pantoyl lactone (ee > 97%) is obtained by stereoselective reduction of ketopantoate with resting cells of anaerobically grown Proteus vulgaris or Proteus mirabilis. Benzyl-viologen or safranine T have been used as electron mediators.
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Velluz,Joly
, (1946)
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Optical Resolution of (R,S)-Pantolactone through Amide Formation
Fizet, Christian
, p. 404 - 409 (1986)
The optical resolution of (RS)-pantolactone (1) is carried out through formation of diastereomeric amides.These are separated by a single hot washing with CH2Cl2 or CHCl3.The used asymmetric amine, (1R)-3-endo-aminoborneol (4), is readily accessible and can be recovered almost quantitatively after resolution.
Industrial kinetic resolution ofd,l-pantolactone by an immobilized whole-cell biocatalyst
Huang, Liu-Nv,Luo, Wen-Fang,Tang, Yi-Bin,Yang, Liu,Zhang, Qiu-Hua
, p. 30373 - 30376 (2021/10/20)
Immobilized whole-cells ofPichia pastorisharboring recombinantd-lactonase were entrapped in calcium alginate gels and used as an efficient biocatalyst for catalytic kinetic resolution ofd,l-pantolactone. The immobilized whole-cell biocatalyst exhibited good catalytic stability, which was applied for stereospecific hydrolysis ofd-pantolactone for up to 56 repeated batch reactions without obvious loss in the catalytic activity and enantioselectivity.
Catalyst Repurposing Sequential Catalysis by Harnessing Regenerated Prolinamide Organocatalysts as Transfer Hydrogenation Ligands
Bourgeois, Frederic,Medlock, Jonathan A.,Bonrath, Werner,Sparr, Christof
supporting information, p. 110 - 115 (2019/12/30)
A catalyst repurposing strategy based on a sequential aldol addition and transfer hydrogenation giving access to enantiomerically enriched α-hydroxy-γ-butyrolactones is described. The combination of a stereoselective, organocatalytic step, followed by an efficient catalytic aldehyde reduction induces an ensuing lactonization to provide enantioenriched butyrolactones from readily available starting materials. By capitalizing from the capacity of prolineamides to act as both an organocatalyst and a transfer hydrogenation ligand, catalyst repurposing allowed the development of an operationally simple, economic, and efficient sequential catalysis approach.
Peptide-Catalyzed Highly Asymmetric Cross-Aldol Reaction of Aldehydes to Biomimetically Synthesize 1,4-Dicarbonyls
Da, Chao-Shan,Du, Zhi-Hong,Qin, Wen-Juan,Tao, Bao-Xiu,Wang, Pei,Xu, Yan-Li,Yuan, Meng
supporting information, (2020/06/08)
β-Turn tetrapeptides were demonstrated to catalyze asymmetric aldol reaction of α-branched aldehydes and α-carbonyl aldehydes, i.e. glyoxylates and α-ketoaldehydes, to biomimetically synthesize acyclic all-carbon quaternary center-bearing 1,4-dicarbonyls in high yield and excellent enantioselectivity under mild conditions. The spatially restricted environment of the tetrapeptide warrants high enantioselectivity and yield with broad substrates. Using this protocol, (R)-pantolactone, the key intermediate of vitamin B5, was readily accessed in a practical, efficient, and environmentally benign process from inexpensive starting materials.