173828-64-3Relevant articles and documents
Evaluation of the performance of differently immobilized recombinant lipase B from Candida antarctica preparations for the synthesis of pharmacological derivatives in organic media
Manoel, Evelin A.,Robert, Julia M.,Pinto, Martina C. C.,MacHado, Antonio C. O.,Besteti, Marina D.,Coelho, Maria Alice Z.,Simas, Alessandro B. C.,Fernandez-Lafuente, Roberto,Pinto, Jose Carlos,Freire, Denise M. G.
, p. 4043 - 4052 (2016)
This paper shows the production of lipase B from Candida antarctica (LIPB) after cloning the gene that encoded it in Pichia pastoris using PGK as a constitutive promoter. The production of the lipase is lower using this strategy but it avoids the use of i
Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
, p. 172 - 181 (2015/03/05)
The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
Chemoselective alcoholysis/acetolysis of trans-ketals over cis-ketals and its application in the total synthesis of the cellular second messenger, d-myo-inositol-1,4,5-trisphosphate
Vidyasagar, Adiyala,Pathigoolla, Atchutarao,Sureshan, Kana M.
, p. 5443 - 5453 (2013/09/02)
The involvement of natural phosphoinositols in various cellular signalling processes and the use of synthetic inositol derivatives in catalysis, supramolecular chemistry, natural product synthesis etc. gave momentum to myo-inositol chemistry. The presence of six secondary hydroxyl groups necessitates efficient protection-deprotection strategies for the synthesis of inositol derivatives. An important strategy for the initial protection of myo-inositol is the di-ketalization, which gives a mixture of three diketals, each having both cis-fused and trans-fused ketals. It is important to have methodologies either to selectively hydrolyze one of the two ketals or to convert one of the two acid labile ketals to an orthogonal base labile protecting group. By exploiting the difference in strain between trans-ketals and cis-ketals, we developed two operationally simple, high yielding methodologies for the chemoselective hydrolysis/acetolysis of trans-ketals (both isopropylidene and cyclohexylidene) of inositols, leaving the cis-ketal undisturbed, using cheap and easily preparable H2SO 4-silica as the catalyst. Also, terminal ketal moieties of carbohydrates and acyclic polyols could be selectively hydrolyzed/acetolyzed leaving the internal ketals intact. The use of methanol as the solvent leads to chemoselective alcoholysis but the use of DCM and acetic anhydride leads to chemoselective acetolysis. Applying this methodology, a short synthesis of d-myo-inositol-1,4,5-trisphosphate has been achieved. The Royal Society of Chemistry.
Kinetic resolution of (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo- inositol by lipases: An experimental and theoretical study on the reaction of a key precursor of chiral inositols
Simas, Alessandro Bolis Costa,Silva, Angelo Amaro Theodoro Da,Cunha, Aline Gomes,Assumpcao, Rafael Silva,Hoelz, Lucas Villas Boas,Neves, Bianca Cruz,Galvao, Teca Calcagno,Almeida, Rodrigo Volcan,Albuquerque, Magaly Girao,Freire, Denise Maria Guimaraes,De Alencastro, Ricardo Bicca
experimental part, p. 32 - 40 (2012/02/03)
The study on kinetic resolution of two myo-inositol derivatives by lipases is reported. Treatment of the triether derivative, (±)-1,2-O- isopropylidene-3,5,6-tri-O-benzyl-myo-inositol, with acylating agents in the presence of different lipases did not aff
Direct selective and controlled protection of multiple hydroxyl groups in polyols via iterative regeneration of stannylene acetals
Simas, Alessandro B.C.,da Silva, Angelo A.T.,dos Santos Filho, Tarcizio J.,Barroso, Pedro T.W.
supporting information; experimental part, p. 2744 - 2746 (2009/09/25)
A direct selective protection (O-benzylation) of two or more hydroxyl groups in polyols displaying diverse structural patterns was made possible by the establishment of conditions that enable an efficient turnover for the Bu2Sn group, initially
Divergent synthesis of all possible optically active regioisomers of myo-inositol mono- and bisphosphates
Seo, Kyung-Chang,Yu, Seok-Ho,Chung, Sung-Kee
, p. 305 - 327 (2008/02/12)
All possible optically active regioisomers of myo-inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IRns) as key intermediates. A series of procedures including Novozym 435 cata
AKT INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF
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Page 10, (2010/02/06)
Disclosed are inhibitors of the serine/threonine kinase Akt, pharmaceutical compositions comprising such inhibitors, and a method of preventing or treating a disease or condition in an animal by the use of such inhibitors. The Akt inhibitors have the form
Synthesis of three enantiomeric pairs of scyllo-inositol phosphate and molecular interactions between all possible regioisomers of scyllo-inositol phosphate and inositol 1,4,5-trisphosphate 3-kinase
Kwon, Yong-Uk,Im, Jungkyun,Choi, Gildon,Kim, Young-Soo,Choi, Kwan Yong,Chung, Sung-Kee
, p. 2981 - 2984 (2007/10/03)
scyllo-Inositol phosphates, which are among the stereoisomers of myo-inositol phosphate, can have 15 possible regioisomers including three enantiomeric pairs: scyllo-I(1,2)P2, scyllo-I(1,2,4)P3, scyllo-I(1,2,3,4)P4. We her
A more convenient and general procedure for O-monobenzylation of diols via Stannylenes: A critical reevaluation of the Bu2SnO method
Simas, Alessandro B. C.,Pais, Karla C.,Da Silva, Angelo A. T.
, p. 5426 - 5428 (2007/10/03)
A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.
Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol
Kwon, Yong-Uk,Lee, Changgook,Chung, Sung-Kee
, p. 3327 - 3338 (2007/10/03)
Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.
