6033-32-5Relevant academic research and scientific papers
A simple synthesis of 6-hydroxynorleucine based on the rearrangement of an N-nitrosodichloroacetamide
McCarthy, Blaine G.,Macarthur, Nicholas S.,Jakobsche, Charles E.
, p. 502 - 504 (2016/01/12)
6-Hydroxynorleucine is a versatile chemical intermediate that has found broad use in target-oriented syntheses of numerous biologically active molecules. Despite its widespread use, and despite the various strategies that have been reported for its prepar
Nitrilases, nucleic acids encoding them and methods for making and using them
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Page/Page column 52; 53, (2016/01/09)
The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.
KDM1A INHIBITORS FOR THE TREATMENT OF DISEASE
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Paragraph 0288, (2014/10/18)
Disclosed herein are new compounds and compositions and their application as pharmaceuticals for the treatment of diseases. Methods of inhibition of KDMIA, and methods of increasing gamma globin gene expression in a human or animal subject are also provided for the treatment diseases such as sickle cell disease.
Asymmetric synthesis of l-6-hydroxynorleucine from 2-keto-6-hydroxyhexanoic acid using a branched-chain aminotransferase
Seo, Young-Man,Kim, Aran,Bea, Han-Seop,Lee, Sang-Hyeup,Yun, Hyungdon
scheme or table, p. 171 - 176 (2012/06/30)
l-6-Hydroxynorleucine was synthesized from 2-keto-6-hydroxyhexanoic acid using branched-chain aminotransferase from Escherichia coli with l-glutamate as an amino donor. Since the branched-chain aminotransferase was severely inhibited by 2-ketoglutarate, the branched-chain aminotransferase reaction was coupled with aspartate aminotransferase and pyruvate decarboxylase. Aspartate aminotransferase converted the inhibitory 2-ketoglutarate back to l-glutamate by using l-aspartate as an amino donor. On the other hand, pyruvate decarboxylase further shifted the reaction equilibrium towards l-6-hydroxynorleucine through decarboxylation of pyruvate to acetaldehyde. The concerted action of the three enzymes significantly enhanced the yield compared to that of branched-chain aminotransferase alone. In the coupled reaction, 90.2 mM l-6-hydroxynorleucine (> 99% ee) was produced from 100 mM 2-keto-6-hydroxyhexanoic acid, whereas in a single branched-chain aminotransferase reaction only 22.5 mM l-6-hydroxynorleucine (> 99% ee) was produced.
An alternative total synthesis of pentosidine
Liu, Yahua,Zhang, Weihan,Sayre, Lawrence M.
experimental part, p. 426 - 433 (2011/06/22)
Pentosidine, a fluorescent advanced glycation endproduct that serves as a biomarker of diabetic complications, kidney dysfunction, oxidative stress, and aging and age-related diseases, was synthesized from 2,3-diaminopyridine and benzyloxycarbonyl (Cbz) p
Selective inhibitors of plasmepsin II of Plasmodium falciparum on the basis of pepstatin
Rumsh,Mikhailova,Mikhura,Prudchenko,Chikin,Mikhaleva,Kaliberda,Dergousova,Mel'Nikov,Formanovskii
experimental part, p. 660 - 667 (2009/04/07)
A number of new inhibitors of plasmepsin II (PlmII) Plasmodium falciparum, which was one of the key factors of survival of malarial parasite, was synthesized. The inhibitors were analogues of pepstatin with different substitutions for the alanine residue.
Synthesis of 7,6-fused bicyclic lactams for use as beta-turn mimics
Morales, Omar,Seide, Wesley,Watson, Samuel
, p. 965 - 973 (2007/10/03)
An improved synthesis of the 7,6-fused bicyclic lactam is presented starting from readily available chiral starting materials. (S)-allylglycine is protected as the phthalimide derivative and coupled with (S)-2-amino-6- hydroxyhexanoic acid methyl ester. Oxidation of the hydroxyl group to the aldehyde followed by enamide synthesis and acyl iminium ion cyclization provide the bicyclic system as a single diastereomer in good overall yield. Copyright Taylor & Francis Group, LLC.
Process for producing hydroxyamino acid derivative
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Page 4, (2008/06/13)
Provided is a method of preparing a hydroxyamino acid derivative, particularly in an optically active form thereof with high efficiency. Specifically, provided is a method of preparing hydroxyamino acid derivatives represented by Formula (I) or salts ther
Biocatalytic synthesis of chiral intermediates for antiviral and antihypertensive drugs
Patel, Ramesh N.
, p. 1275 - 1281 (2007/10/03)
The chiral intermediate (1S,2R) [3-chloro-2-hydroxy-1-(phenylmethyl)propyl] carbamic acid, 1,1-dimethyl-ethyl ester 2a was prepared for the total synthesis of a human immunodeficiency virus protease inhibitor, BMS-186318. The stereoselective reduction of (1S) [3-chloro-2-oxo-1(phenylmethyl)propyl] carbamic acid, 1,1-dimethylethyl ester 1 was carried out using microbial cultures, among which Streptomyces nodosus SC 13149 efficiently reduced 1 to 2a. A reaction yield of 80%, enantiomeric excess (e.e.) of 99.8%, and diastereomeric purity of 99% were obtained for chiral alcohol 2a. Chiral L-6-hydroxy norleucine 3, an intermediate in the synthesis of antihypertensive drug, was prepared by reductive amination of 2-keto-6-hydroxyhexanoic acid 4 using beef liver glutamate dehydrogenase. The cofactor NADH required for this reaction was regenerated using glucose dehydrogenase from Bacillus sp. A reaction yield of 80% and e.e. of 99.5% were obtained for L-6-hydroxynorleucine 3. To avoid the lengthy chemical synthesis of the ketoacid, a second route was developed in which racemic 6-hydroxynorleucine [readily available from hydrolysis of 5-(4-hydroxybutyl) hydantoin 5] was treated with D-amino acid oxidase from Trigonopsis variabilis to selectively convert the D-isomer of racemic 6-hydroxynorleucine to 2-keto-6-hydroxyhexanoic acid 4 and L-6-hydroxynorleucine 3. Subsequently, the 2-keto-6-hydroxyhexanoic acid 4 was converted to L-6-hydroxynorleucine by reductive amination using glutamate dehydrogenase. A reaction yield of 98% and an e.e. of 99.5% were obtained.
