Stereodivergent Synthesis of 3‐Hydroxyprolines and 3‐Hydroxypipecolic Acids via Ketoreductase‐Catalyzed Dynamic Kinetic Reduction

[1]  D. Tirrell,et al.  4S-Hydroxylation of Insulin at ProB28 Accelerates Hexamer Dissociation and Delays Fibrillation. , 2017, Journal of the American Chemical Society.

[2]  Nicholas J Agard,et al.  Synthesis of the GPR40 Partial Agonist MK-8666 through a Kinetically Controlled Dynamic Enzymatic Ketone Reduction. , 2016, Organic letters.

[3]  D. Berkowitz,et al.  Exploiting Enzymatic Dynamic Reductive Kinetic Resolution (DYRKR) in Stereocontrolled Synthesis. , 2015, Advanced synthesis & catalysis.

[4]  J. Bäckvall,et al.  Chemoenzymatic Dynamic Kinetic Resolution: A Powerful Tool for the Preparation of Enantiomerically Pure Alcohols and Amines , 2015, Journal of the American Chemical Society.

[5]  Steven P. Miller,et al.  Practical and cost-effective manufacturing route for the synthesis of a β-lactamase inhibitor. , 2014, Organic letters.

[6]  R. Schwartz,et al.  Discovery and development of first in class antifungal caspofungin (CANCIDAS®)--a case study. , 2014, Natural product reports.

[7]  D. Eyre,et al.  Collagen prolyl 3-hydroxylation: a major role for a minor post-translational modification? , 2013, Connective tissue research.

[8]  Wolfgang Hüttel Biocatalytic Production of Chemical Building Blocks in Technical Scale with α‐Ketoglutarate‐Dependent Dioxygenases , 2013 .

[9]  J. Cossy,et al.  Synthesis of 3‐Hydroxypipecolic Acids , 2013 .

[10]  Sangit Kumar,et al.  A Highly Efficient Copper-Catalyzed Method for the Synthesis of 2-Hydroxybenzamides in Water , 2012 .

[11]  M. Rudd,et al.  Discovery of MK-5172, a Macrocyclic Hepatitis C Virus NS3/4a Protease Inhibitor. , 2012, ACS medicinal chemistry letters.

[12]  E. J. Sorensen,et al.  Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine , 2007 .

[13]  S. Ruchirawat,et al.  Ziziphine N, O, P and Q, new antiplasmodial cyclopeptide alkaloids from Ziziphus oenoplia var. brunoniana , 2005 .

[14]  Carol M. Taylor,et al.  The impact of pyrrolidine hydroxylation on the conformation of proline-containing peptides. , 2005, The Journal of organic chemistry.

[15]  R. Raines,et al.  Effect of 3-hydroxyproline residues on collagen stability. , 2003, Journal of the American Chemical Society.

[16]  K. Kang,et al.  Efficient synthesis of 3-hydroxyprolines and 3-hydroxyprolinols from sugars , 2001 .

[17]  Robert M. Williams,et al.  Total Synthesis of (-)-Tetrazomine and Determination of Its Stereochemistry. , 2001, Angewandte Chemie.

[18]  J. Wang,et al.  Intramolecular N–H insertion of α-diazocarbonyls catalyzed by Cu(acac)2: An efficient route to derivatives of 3-oxoazetidines, 3-oxopyrrolidines and 3-oxopiperidines , 1999 .

[19]  C. Greck,et al.  Rapid Asymmetric Synthesis of Highly Functionalized C5 Chiral Synthons. Practical Preparation of trans-3-Hydroxy-D-Proline , 1998 .

[20]  J. Durand,et al.  Reductive cyanation: A key step for a short synthesis of (−)-(2S,3S)-3-hydroxyproline , 1998 .

[21]  J. Gillard,et al.  Preparation of (2S,4R)-4-Hydroxypipecolic Acid and Derivatives , 1996 .

[22]  J. Mulzer,et al.  Total Synthesis of cis- and trans-3-Hydroxy-D-proline and (+)-Detoxinine. , 1996, The Journal of organic chemistry.

[23]  C. Herdeis,et al.  Chiral pool synthesis of trans-(2S3S)-3-hydroxyproline and castanodiol from S-pyroglutamic acid. , 1994 .

[24]  D. Haigh,et al.  New members of the chiral pool: β-Hydroxypiperidine carboxylates from Baker's yeast reductions of the corresponding keto-esters , 1993 .

[25]  C. Sih,et al.  A chemoenzymatic synthesis of (+)-castanospermine , 1990 .

[26]  J. Clardy,et al.  Total synthesis of 3(S)-carboxy-4(S)-hydroxy-2,3,4,5-tetrahydropyridazine, an unusual amino acid constituent of luzopeptin A , 1989 .

[27]  J. Cooper,et al.  Expedient syntheses of (+)-cis-(2R,3S)-3-hydroxyproline and (–)-(1S,5S)-2-oxa-6-azabicyclo[3.3.0]octan-3-one (the Geissman–Waiss lactone): formal enantioselective syntheses of (–)-retronecine and related pyrrolizidine alkaloids , 1988 .

[28]  J. C. Sheehan,et al.  The Synthesis ofcis- andtrans-3-Hydroxy-L-proline, Two New Amino Acids from the Antibiotic Telomycin , 1963 .