95341-65-4Relevant academic research and scientific papers
Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles
Smart, Tristan J.,Hamed, Refaat B.,Claridge, Timothy D.W.,Schofield, Christopher J.
supporting information, (2019/11/26)
Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable, as yet largely untapped, potential for amino acid hydroxylases and other 2OG oxygenases in biocatalysis.
Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases
Hara, Ryotaro,Uchiumi, Naoko,Okamoto, Naoko,Kino, Kuniki
, p. 1384 - 1388 (2015/07/20)
We evaluated the substrate specificities of four proline cis-selective hydroxylases toward the efficient synthesis of proline derivatives. In an initial evaluation, 15 proline-related compounds were investigated as substrates. In addition to L-proline and L-pipecolinic acid, we found that 3,4-dehydro-L-proline, L-azetidine-2-carboxylic acid, cis-3-hydroxy-L-proline, and L-thioproline were also oxygenated. Subsequently, the product structures were determined, revealing cis-3,4-epoxy-L-proline, cis-3-hydroxy-L-azetidine-2-carboxylic acid, and 2,3-cis-3,4-cis-3,4-dihydroxy-L-proline.
Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)
Garcia, Ariel Lázaro L.,Correia, Carlos Roque D.
, p. 1553 - 1557 (2007/10/03)
cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.
Facile synthesis of 3,4-dihydroxyprolines as an application of the L- threonine aldolase-catalyzed aldol reaction
Fujii, Mikio,Miura, Tsuyoshi,Kajimoto, Tetsuya,Ida, Yoshiteru
, p. 1046 - 1048 (2007/10/03)
A new facile synthesis of 3,4-dihydroxyprolines was attained by taking advantage of the L-threonine aldolase, which catalyzes the aldol condensation reaction of aldehydes with glycine affording β-hydroxy-α-L-amino acids.
Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate
Pohlit, Adrian M.,Correia, Carlos Roque D.
, p. 2321 - 2325 (2007/10/03)
A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrro
Straightforward Synthesis of Pyrrolidine Glycosidase Inhibitors via Asymmetric Hetero-Diels-Alder Reaction
Defoin, Albert,Sifferlen, Thierry,Streith, Jacques
, p. 1294 - 1296 (2007/10/03)
Base-catalysed rearrangement of the oxazine-carboxylate 8, obtained from pentadienoic acid 4 by asymmetric hetero-Diels-Alder reaction followed by simple chemical transformations, led to the protected trihydroxy-proline 9. Using various reduction conditions, the potent glycosidase inhibitors 1,4-dideoxy-1,4-imino-D-lyxitol D-1 and 1,4-dideoxy-1,4-imino-L-ribitol L-2 were obtained.
(±)-4-amino-4,5-dideoxyribose, (±)-4-amino-4-deoxyerythrose, and (±)-dihydroxyproline derivatives from N-dienyl-γ-lactams
Behr,Defoin,Mahmood,Streith
, p. 1166 - 1177 (2007/10/02)
Hetero-Diels-Alder cycloaddition of acylnitroso dienophile 4 with the N-(butadienyl)pyrrolidinone derivatives 2a,b led with complete regioselectivity to the oxazine adducts 5a,b. Sequential osmylation, protection of the ensuing glycol, and reduction of th
DIPOLAR CYCLOADDITION REACTIONS OF AZOMETHINE YLIDES FOR THE SYNTHESIS OF POLYHYDROXYPYRROLIDINES AS POTENTIAL ENZYMATIC INHIBITORS
Hassan, Mohamed E.
, p. 7 - 9 (2007/10/02)
Tosyl and benzyl azomethine ylides generated from the corresponding aziridines under thermal and photochemical conditions, were trapped by dipolar cycloaddition reaction with vinylene carbonate.The methoxycarbonyl group in the pyrrolidines obtained was re
Synthesis of (3S,4S)-3,4-dihydroxyprolines from L-tartaric acid
Arakawa,Yoshifuji
, p. 2219 - 2224 (2007/10/02)
Natural (2S,3S,4S)-3,4-dihydroxyproline (1) and the new (2R,3S,4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.
Ketene Dithioacetals as 1,3-Dipolarophiles. Applications to the Synthesis of Cyclic Amino Acids
Moss, William O.,Bradbury, Robert H.,Hales, Neil J.,Gallagher, Timothy
, p. 51 - 53 (2007/10/02)
Intramolecular azide cycloaddition reactions of ketene dithioacetals provide a new route to cyclic amino acids and a stereoselective synthesis of (2S,3S,4R)-3,4-dihydroxyproline (14) based on this methodology is described.
