18-Norbeyeran-17-oic acid, 3-oxo-, methyl ester
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05609 |
| CAS | 887227-67-0 |
| Molecular Weight | 316.43 |
| Molecular Formula | C20H28O3 |
Online Inquiry
Specification
| Synonyms | 3-oxo-18-Norbeyeran-17-oic acid methyl ester |
| IUPAC Name | methyl (4R,4aR,6aR,9R,11aS,11bR)-4,11b-dimethyl-3-oxo-2,3,4,4a,5,6,10,11,11a,11b-decahydro-6a,9-methanocyclohepta[a]naphthalene-9(1H)-carboxylate |
Properties
| Boiling Point | 413.4±45.0°C (Predicted) |
| Density | 1.13±0.1 g/cm3 (Predicted) |
Reference Reading
1. Bioconversion of Phytosterols to 9-Hydroxy-3-Oxo-4,17-Pregadiene-20-Carboxylic Acid Methyl Ester by Enoyl-CoA Deficiency and Modifying Multiple Genes in Mycolicibacterium neoaurum
Chenyang Yuan, Shikui Song, Jianxin He, Jingxian Zhang, Xiangcen Liu, Eliana L Pena, Junsong Sun, Jiping Shi, Zhengding Su, Baoguo Zhang Appl Environ Microbiol. 2022 Nov 22;88(22):e0130322. doi: 10.1128/aem.01303-22. Epub 2022 Oct 26.
Steroid drug precursors, including C19 and C22 steroids, are crucial to steroid drug synthesis and development. However, C22 steroids are less developed due to the intricacy of the steroid metabolic pathway. In this study, a C22 steroid drug precursor, 9-hydroxy-3-oxo-4,17-pregadiene-20-carboxylic acid methyl ester (9-OH-PDCE), was successfully obtained from Mycolicibacterium neoaurum by 3-ketosteroid-Δ1-dehydrogenase and enoyl-CoA hydratase ChsH deficiency. The production of 9-OH-PDCE was improved by the overexpression of 17β-hydroxysteroid dehydrogenase Hsd4A and acyl-CoA dehydrogenase ChsE1-ChsE2 to reduce the accumulation of by-products. The purity of 9-OH-PDCE in fermentation broth was improved from 71.7% to 89.7%. Hence, the molar yield of 9-OH-PDCE was improved from 66.7% to 86.7%, with a yield of 0.78 g/L. Furthermore, enoyl-CoA hydratase ChsH1-ChsH2 was identified to form an indispensable complex in Mycolicibacterium neoaurum DSM 44704. IMPORTANCE C22 steroids are valuable precursors for steroid drug synthesis, but the development of C22 steroids remains unsatisfactory. This study presented a strategy for the one-step bioconversion of phytosterols to a C22 steroid drug precursor, 9-hydroxy-3-oxo-4,17-pregadiene-20-carboxylic acid methyl ester (9-OH-PDCE), by 3-ketosteroid-Δ1-dehydrogenase and enoyl-CoA hydratase deficiency with overexpression of 17β-hydroxysteroid dehydrogenase acyl-CoA dehydrogenase in Mycolicibacterium. The function of the enoyl-CoA hydratase ChsH in vivo was revealed. Construction of the novel C22 steroid drug precursor producer provided more potential for steroid drug synthesis, and the characterization of the function of ChsH and the transformation of steroids further revealed the steroid metabolic pathway.
2. A Plurizyme with Transaminase and Hydrolase Activity Catalyzes Cascade Reactions
Sergi Roda, Laura Fernandez-Lopez, Marius Benedens, Alexander Bollinger, Stephan Thies, Julia Schumacher, Cristina Coscolín, Masoud Kazemi, Gerard Santiago, Christoph G W Gertzen, Jose L Gonzalez-Alfonso, Francisco J Plou, Karl-Erich Jaeger, Sander H J Smits, Manuel Ferrer, Víctor Guallar Angew Chem Int Ed Engl. 2022 Sep 12;61(37):e202207344. doi: 10.1002/anie.202207344. Epub 2022 Aug 4.
Engineering dual-function single polypeptide catalysts with two abiotic or biotic catalytic entities (or combinations of both) supporting cascade reactions is becoming an important area of enzyme engineering and catalysis. Herein we present the development of a PluriZyme, TR2 E2 , with efficient native transaminase (kcat : 69.49±1.77 min-1 ) and artificial esterase (kcat : 3908-0.41 min-1 ) activities integrated into a single scaffold, and evaluate its utility in a cascade reaction. TR2 E2 (pHopt : 8.0-9.5; Topt : 60-65 °C) efficiently converts methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate into 3-(R)-amino-4-(2,4,5-trifluorophenyl)butanoic acid, a crucial intermediate for the synthesis of antidiabetic drugs. The reaction proceeds through the conversion of the β-keto ester into the β-keto acid at the hydrolytic site and subsequently into the β-amino acid (e.e. >99 %) at the transaminase site. The catalytic power of the TR2 E2 PluriZyme was proven with a set of β-keto esters, demonstrating the potential of such designs to address bioinspired cascade reactions.
3. Analysis of potential phenylacetone precursors (ethyl 3-oxo-2-phenylbutyrate, methyl 3-oxo-4-phenylbutyrate, and ethyl 3-oxo-4-phenylbutyrate) by gas chromatography/mass spectrometry and their conversion to phenylacetone
Kenji Tsujikawa, Yuki Okada, Hiroki Segawa, Kenji Kuwayama, Tadashi Yamamuro, Tatsuyuki Kanamori, Yuko T Iwata Drug Test Anal. 2022 Mar;14(3):439-449. doi: 10.1002/dta.3169. Epub 2021 Oct 21.
Methyl 3-oxo-2-phenylbutyrate (MAPA) is a recently circulating precursor of phenylacetone (P2P), a precursor of amphetamine and methamphetamine. MAPA has a hybrid chemical structure of acetoacetic acid ester and P2P. Acetoacetic acid ester is de-esterified and decarboxylated to give the ketone by heating under acidic conditions; therefore, MAPA is presumed to be converted to P2P by such treatment. Considering that ethyl 3-oxo-2-phenylbutyrate (EAPA), methyl 3-oxo-4-phenylbutyrate (MGPA), and ethyl 3-oxo-4-phenylbutyrate (EGPA) have the same chemical features as MAPA, these three compounds are potential P2P precursors. The authors examined the analysis of these compounds by gas chromatography-mass spectrometry (GC-MS) and their conversion to P2P by heating under acidic and basic conditions. These compounds were remarkably decomposed into P2P during GC-MS analysis regardless of the injection method and injector temperature. EAPA and EGPA also caused ester exchange to methyl ester by injection of methanol solution. P2P production and transesterification were almost prevented by methoxime derivatization. These compounds were converted to P2P by heating under acidic conditions. The reaction of MGPA and EGPA proceeded quicker than that of EAPA. The important by-product associated with the reaction was phenylacetylcarbinol (formed from EAPA and MGPA), which will be converted to (pseudo)ephedrine, important methamphetamine impurities. By heating under basic conditions, MGPA and EGPA were converted to P2P but EAPA was mainly converted to phenylacetic acid. In the future, when these compounds are in circulation, our study will be useful for identifying and elucidating the synthetic method of P2P.
Recommended Products
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
