475630-67-2Relevant academic research and scientific papers
LACK OF GLYCOSIDASE INHIBITION BY, AND ISOLATION FROM XANTHOCERCIS ZAMBESIACA (LEGUMINOSAE) OF, 4-O-(&β-D-GLUCOPYRANOSYL)-FAGOMINE , A NOVEL GLUCOSIDE OF POLYHYDROXYLATED PIPERIDINE ALKALOID
Evans, Stephen V.,Hayman, Alison R.,Fellows, Linda E.,Shing, Tony K. M.,Derome, Andrew E.,Fleet, George W. J.
, p. 1465 - 1468 (1985)
A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn.Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor the fagomine (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.
Silicon-mediated asymmetric synthesis of fagomine and 3,4-di-epi-fagomine
Kundu, Pintu K.,Ghosh, Sunil K.
, p. 1090 - 1096 (2011)
The synthesis of d-fagomine and its stereoisomer, d-3,4-di-epi-fagomine has been achieved from C2-symmetric 3,4-bis-silyl substituted adipic acid di-oxazolidin-2-one derivatives via stereocontrolled azidation and silicon to hydroxyl conversion as the key steps. The Evans oxazolidin-2-one controlled the stereochemical outcome of the azidation which supersedes the directing effects of the silyl substituent.
N-Containing sugars from Morus alba and their glycosidase inhibitory activities
Asano, Naoki,Oseki, Kengo,Tomioka, Emiko,Kizu, Haruhisa,Matsui, Katsuhiko
, p. 243 - 256 (1994)
The reexamination of N-containing sugars from the roots of Morus alba by improved purification procedures led to the isolation of eighteen N-containing sugars, including seven that were isolated from the leaves of Morus bombycis.These N-containing sugars
Concise and highly stereoselective syntheses of D-fagomine and 2-epi-fagomine
Kallam, Srinivasa Reddy,Datrika, Rajender,Khobare, Sandip R.,Gajare, Vikas S.,Rajana, Nagaraju,Mohan, H. Rama,Babu, J. Moses,Siddaiah,Pratap
, p. 1351 - 1353 (2018/03/23)
Highly stereoselective total syntheses of polyhydroxylated piperidines D-fagomine and 2-epi-fagomine have been developed starting from 3,4,6-tri-O-benzyl-D-glucal which is a derivative of D-Glucose. Key steps in the synthesis of these azasugars involved N-Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N-Boc deprotection.
L -Rhamnulose-1-phosphate Aldolase from Thermotoga maritima in Organic Synthesis: One-Pot Multistep Reactions for the Preparation of Imino- and Nitrocyclitols
Oroz-Guinea, Isabel,Hernández, Karel,Campsbres, Flora,Guérard-Hélaine, Christine,Lemaire, Marielle,Clapés, Pere,García-Junceda, Eduardo
, p. 1951 - 1960 (2015/06/02)
Rhamnulose-1-phosphate aldolase from Thermotoga maritima (Rhu1PATm) has been recently cloned and characterised. This hyperthermophilic enzyme offers intriguing possibilities for practical catalysis. This is due to its high stability under extreme reaction
Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids
Marjanovic, Jasna,Ferjancic, Zorana,Saicic, Radomir N.
, p. 6784 - 6789 (2015/08/24)
The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyz
A PROCESS FOR SYNTHESIS OF PIPERIDINE ALKALOIDS
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Paragraph 0046; 0047, (2015/11/27)
The present invention discloses a process for synthesis of piperidine alkaloids selected from fagomine, 4-epi-fagomine and nojirimycin from tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal.
Transforming flask reaction into cell-based synthesis: Production of polyhydroxylated molecules via engineered Escherichia coli
Wei, Mohui,Li, Zijie,Li, Tiehai,Wu, Baolin,Liu, Yunpeng,Qu, Jingyao,Li, Xu,Li, Lei,Cai, Li,Wang, Peng George
, p. 4060 - 4065 (2015/11/11)
Dihydroxyacetone phosphate (DHAP)-dependent aldolases have been intensively studied and widely used in the synthesis of carbohydrates and complex polyhydroxylated molecules. However, strict specificity toward donor substrate DHAP greatly hampers their synthetic utility. Here, we transformed DHAP-dependent aldolases-mediated by in vitro reactions into bioengineered Escherichia coli (E. coli). Such flask-to-cell transformation addressed several key issues plaguing in vitro enzymatic synthesis: (1) it solves the problem of DHAP availability by in vivo-hijacking DHAP from the glycolysis pathway of the bacterial system, (2) it circumvents purification of recombinant aldolases and phosphatase, and (3) it dephosphorylates the resultant aldol adducts in vivo, thus eliminating the additional step for phosphate removal and achieving in vivo phosphate recycling. The engineered E. coli strains tolerate a wide variety of aldehydes as acceptor and provide a set of biologically relevant polyhydroxylated molecules in gram scale.
A concise synthesis of N-substituted fagomine derivatives and the systematic exploration of their α-glycosidase inhibition
Jiang, Fu-Xiang,Liu, Qiao-Zhen,Zhao, Dan,Luo, Cui-Ting,Guo, Cui-Ping,Ye, Wen-Cai,Luo, Cheng,Chen, Heru
, p. 211 - 222 (2014/04/03)
A novel and concise scheme has been developed successfully for the syntheses of N-substituted fagomine derivatives. The transformation of lactone (2) to 1,5-diol (3) was carried on with high yield (93-95%). The cyclization of 4 to 5 is a high stereoselect
Asymmetric syntheses of (-)-3-epi-fagomine, (2 R,3 S,4 R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids
Csatayov, Kristna,Davies, Stephen G.,Fletcher, Ai M.,Ford, J. Gair,Klauber, David J.,Roberts, Paul M.,Thomson, James E.
, p. 10932 - 10944 (2015/01/09)
A range of enantiopure polyhydroxylated piperidines, including (2R,3S,4R)-dihydroxypipecolic acid, (-)-3-epi-fagomine, (2S,3S,4R)-dihydroxyhomopipecolic acid, (2S,3R,4R)-dihydroxyhomopipecolic acid, and two trihydroxy-substituted homopipecolic acids, have been prepared using diastereoselective olefinic oxidations of a range of enantiopure tetrahydropyridines as the key step. The requisite substrates were readily prepared from tert-butyl sorbate using our diastereoselective hydroamination or aminohydroxylation protocols followed by ring-closing metathesis. After diastereoselective olefinic oxidation of the resultant enantiopure tetrahydropyridines and deprotection, enantiopure polyhydroxylated piperidines were isolated as single diastereoisomers (>99:1 dr) in good overall yield.
