Chemo-Enzymatic Synthesis of Enantiopure ß-Blocker (S)-Metoprolol and Derivatives

被引：3

作者：

Bockmann, Pal L. ^{[1
]}

Jacobsen, Elisabeth E. ^{[1
]}

机构：

[1] Norwegian Univ Sci & Technol NTNU, Dept Chem, Hogskoleringen 5, N-7491 Trondheim, Norway

来源：

TOPICS IN CATALYSIS | 2024年 / 67卷 / 5-8期

关键词：

(S)-Metoprolol; Enantiopure building blocks; Candida antarctica Lipase B; Chiral chromatography; Specific rotation; KINETIC RESOLUTION; METOPROLOL; LIPASE; PROPRANOLOL; PINDOLOL; ALCOHOLS; RACEMATE; RATIO;

D O I：

10.1007/s11244-023-01860-1

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

S)-Metoprolol, ((2 S)-1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol has been synthesised in 99% ee with high yield by a four step chemoenzymatic protocol. Several preparations of Candida antarctica lipase B have been screened in a kinetic resolution of the secondary chlorohydrin 1-chloro-3-(4-(2-methoxyethyl)phenoxy)propan-2-ol. We here report specific rotation values of the enantiopure chlorohydrins from the enzyme catalysed kinetic resolution, in addition to a specific rotation value for (S)-metoprolol, which determines the absolute configuration of the drug, and also the absolute configuration of the chlorohydrin enantiomers.

引用

页码：563 / 571

页数：9

共 50 条

[21] Robust and straightforward chemo-enzymatic enantiopure dipeptide syntheses and diketopiperazines thereof
Pereira, Pedro C.
Arends, Isabel W. C. E.
Sheldon, Roger A.
TETRAHEDRON-ASYMMETRY, 2014, 25 (10-11) : 825 - 832
[22] New chemo-enzymatic approaches for the synthesis of (R)- and (S)-bufuralol
Nagy, Botond
Dima, Norbert
Paizs, Csaba
Brem, Juergen
Irimie, Florin Dan
Tosa, Monica Ioana
TETRAHEDRON-ASYMMETRY, 2014, 25 (18-19) : 1316 - 1322
[23] Chemo-enzymatic synthesis of calcitonin derivatives containing N-linked oligosaccharides
Haneda, K
Inazu, T
Mizuno, M
Iguchi, R
Yamamoto, K
Kumagai, H
Aimoto, S
Suzuki, H
Noda, T
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (11) : 1303 - 1306
[24] New chemo and chemo-enzymatic synthesis of β-benzyl-γ-butyrolactones
Koul, S
Singh, B
Taneja, SC
Qazi, GN
TETRAHEDRON, 2003, 59 (19) : 3487 - 3491
[25] Chemo-enzymatic synthesis of α-terpineol thioacetate and thiol derivatives and their use as flavouring compounds
Bel-Rhlid, Rachid
Rey, Yvette Fleury
Welti, Dieter
Fumeaux, Rene
Moine, Deborah
YEAST, 2015, 32 (01) : 115 - 122
[26] Chemo-enzymatic synthesis of chiral 2-substituted succinic acid derivatives
Bailey, MD
Halmos, T
Adamson, D
Bordeleau, J
Grand-Maître, C
TETRAHEDRON-ASYMMETRY, 1999, 10 (17) : 3285 - 3295
[27] CHEMO-ENZYMATIC SYNTHESIS OF 1′-PHOTOREACTIVE SUCROSE DERIVATIVES VIA ETHER LINKAGE
Tsunekawa, Yuka
Masuda, Katsuyoshi
Muto, Miho
Muto, Yasuyuki
Murai, Yuta
Hashidoko, Yasuyuki
Orikasa, Yoshitake
Oda, Yuji
Hatanaka, Yasumaru
Hashimoto, Makoto
HETEROCYCLES, 2012, 84 (01) : 283 - 290
[28] Chemo-enzymatic synthesis of natural products and their analogs
Kaspar, Felix
Schallmey, Anett
CURRENT OPINION IN BIOTECHNOLOGY, 2022, 77
[29] Biocatalytic and Chemo-Enzymatic Approaches for the Synthesis of Heterocycles
Zhao, Fei
Masci, Domiziana
Tomarelli, Elena
Castagnolo, Daniele
SYNTHESIS-STUTTGART, 2020, 52 (20): : 2948 - 2961
[30] Chemo-enzymatic synthesis of both enantiomers of rugulactone
Reddipalli, Gowrisankar
Venkataiah, Mallam
Fadnavis, Nitin W.
TETRAHEDRON-ASYMMETRY, 2010, 21 (03) : 320 - 324

← 1 2 3 4 5 →