53562-86-0Relevant articles and documents
Neomacrophorin I, II, and III, novel drimenyl cyclohexanes with hydroxylated butanoates from Trichoderma sp. 1212-03
Hirose, Akane,Maeda, Hayato,Tonouchi, Akio,Nehira, Tatsuo,Hashimoto, Masaru
, p. 1458 - 1463 (2014)
Neomacrophorins I (1), II (2), and III (3) were isolated from the culture broth of Trichoderma sp. 1212-03, which was collected at Shirakami Mountainous area in Japan. Structural analyses disclosed that these resemble known macrophorins but possess axial-
Ru coordinated with BINAP in knitting aryl network polymers for heterogeneous asymmetric hydrogenation of methyl acetoacetate
Wang, Tao,Lyu, Yuan,Chen, Xingkun,Li, Cunyao,Jiang, Miao,Song, Xiangen,Ding, Yunjie
, p. 28447 - 28450 (2016)
A facile method for the preparation of heterogeneous asymmetric hydrogenation catalysts was presented. BINAP was knitted with aryl compounds using formaldehyde dimethyl acetal (FDA) as a cross-linker by Friedel-Crafts reaction without any pre-modification. The prepared catalysts showed different catalytic activities, and excellent recyclablilty results could be achieved in asymmetric hydrogenation.
3-Deoxyglucosone reductase in dog adrenal glands. Identification as aldose reductase
Matsuura,Sato,Deyashiki,Nakanishi,Hara
, p. 1765 - 1767 (1995)
3-Deoxyglucosone is one of the major cytotoxic intermediates in the Maillard reaction. Adrenal glands showed the highest NADPH-linked 3- deoxyglucosone reductase activity of dog tissues. The enzyme was purified to homogeneity from the adrenal glands, and demonstrated to be structurally, functionally and immunologically identical with aldose reductase, which comprises about 6% of the salable adrenal proteins.
Synthesis and characterization of a high-purity chiral 5,5'-disulfonato-BINAP ligand and its application in asymmetric hydrogenation of β-keto esters
Jin, Xin,Huang, Sen,Wang, Fan,Zhu, Lin,Song, Hongbing,Xie, Congxia,Yu, Shitao,Li, Shumei
, (2021)
2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) is a widely used chiral phosphine ligand, and the sulfonated BINAP is one of the important water-soluble BINAP derivatives. In this article, we report an improved oleum sulfonation method for the synthesis of the high-purity 5,5′-disulfonato-(S)-BINAP ligand with an industrially acceptable high yield. By optimizing the sulfonation conditions and improving the workup process, the yield of 5,5′-disulfonated products was enhanced to 73 %. Furthermore, an acetonitrile extraction protocol was developed for the purification of sulfonated products by efficiently removing phosphine oxides, by which the content of phosphine oxide can be controlled below 3 %. The structure of 5,5′-disulfonato-(S)-BINAP was characterized with the elemental analysis, FT-IR, 1H NMR, 13C NMR, 31P NMR, 1H-1H COSY, 1H-13C HSQC, 1H-13C HMBC, and HR-MS, which unambiguously confirmed that the sulfo groups are introduced at the 5,5′-position of the binaphthyl ring skeleton in (S)-BINAP. The prepared high-purity 5,5′-disulfonato-(S)-BINAP was evaluated in the Ru-catalyzed asymmetric hydrogenation of β-keto esters, which exhibited high catalytic activity, enantioselectivity and excellent catalytic stability.
Application of robust ketoreductase from Hansenula polymorpha for the reduction of carbonyl compounds
Petrovi?ová, Tatiana,Gyuranová, Dominika,Pl?, Michal,Myrtollari, Kamela,Smonou, Ioulia,Rebro?, Martin
, (2021/02/05)
Enzyme-catalysed asymmetric reduction of ketones is an attractive tool for the production of chiral building blocks or precursors for the synthesis of bioactive compounds. Expression of robust ketoreductase (KRED) from Hansenula polymorpha was upscaled and applied for the asymmetric reduction of 31 prochiral carbonyl compounds (aliphatic and aromatic ketones, diketones and β-keto esters) to the corresponding optically pure hydroxy compounds. Biotransformations were performed with the purified recombinant KRED together with NADP+ recycling glucose dehydrogenase (GDH, Bacillus megaterium), both overexpressed in Escherichia coli BL21(DE3). Maximum activity of KRED for biotransformation of ethyl-2-methylacetoacetate achieved by the high cell density cultivation was 2499.7 ± 234 U g–1DCW and 8.47 ± 0.40 U·mg–1E, respectively. The KRED from Hansenula polymorpha is a very versatile enzyme with broad substrate specificity and high activity towards carbonyl substrates with various structural features. Among the 36 carbonyl substrates screened in this study, the KRED showed activity with 31, with high enantioselectivity in most cases. With several ketones, the Hansenula polymorpha KRED catalysed preferentially the formation of the (R)-secondary alcohols, which is highly valued.
Chiral amino-pyridine-phosphine tridentate ligand, manganese complex, and preparation method and application thereof
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Paragraph 0597-0600; 0603, (2020/07/13)
The invention discloses a chiral amino-pyridine-phosphine tridentate ligand, a manganese complex, and a preparation method and application thereof. The chiral amino-pyridine-phosphine tridentate ligand is shown as a formula II, and the manganese complex of the chiral amino-pyridine-phosphine tridentate ligand can be used for efficiently catalyzing and hydrogenating ketone compounds to prepare chiral alcohol compounds in a high enantioselectivity mode. The chiral amino-pyridine-phosphine tridentate ligand and the manganese complex are simple in synthesis process, good in stability, high in catalytic activity and mild in reaction conditions.
