- Total syntheses of cyclitol based natural products from myo-inositol: brahol and pinpollitol
-
Inositol and their derivatives are important class of biologically active natural products. Among the nine theoretically possible inositols, six are known to occur in nature. Interestingly one or more methyl ethers of these inositols have been isolated fr
- Sureshan, Kana M.,Murakami, Tomohiro,Watanabe, Yutaka
-
-
Read Online
- Establishment of the structure of pinpollitol by total synthesis of the proposed putative structures
-
Proposed structures of pinpollitol, namely 1,4-di-O-methyl-chiro-inositol and 1,3-di-O-methyl-chiro-inositol, have been synthesized from myo-inositol. Racemic 1,4-di-O-methyl-chiro-inositol has been synthesized from the readily available 1,2:4,5-di-O-isop
- Sureshan, Kana M.,Murakami, Tomohiro,Watanabe, Yutaka
-
-
Read Online
- Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
-
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
- Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
-
p. 172 - 181
(2015/03/05)
-
- General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives
-
The D-3-phosphorylated wyo-inositol phospholipids PtdIns(3)P, PtdIns(3,4)P2, PtdIns(3,4,5)P3 and PtdIns(3,5)P2 were synthesised from /yo-inositol orthoformate 8. Key transformations included the regioselective DIBAL- and trimethylaluminium-mediated cleavages of wiyo-inositol orthoformate intermediates and a resolution-protection protocol using the camphor acetals 17. The final reductive debenzylation was effected with Pearlman's catalyst [Pd(OH)J in the presence of sodium hydrogen carbonate. The biological properties of the phospholipids were evaluated against various protein kinases (PKB and PDK-1) in which they played an important activation role.
- Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.
-
p. 923 - 935
(2007/10/03)
-
- Membrane-permeant esters of inositol polyphosphates, chemical syntheses and biological applications
-
Membrane-permeant derivatives of inositol polyphosphates are useful tools for biological studies. Racemic 2,3,6-tri-O-butyryl-myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester(Bt3IP3/AM), myo-inositol 1,4,5-trisphosphate hexakis(acetoxymethyl) ester (IP3/AM), hexakis(propionyloxymethyl) ester (IP3/PM) and hexakis(butyryloxymethyl) ester (IP3/BM) were therefore synthesized. Whereas extracellular application of up to 200 μM of Bt3IP3/AM or IP3/AM to 1321N1 astrocytoma cells failed to mobilize internal calcium, IP3/PM and IP3/BM released internal calcium at concentrations as low os 20 μM and 2 μM, respectively.
- Li, Wenhong,Schultz, Carsten,Llopis, Juan,Tsien, Roger Y.
-
p. 12017 - 12040
(2007/10/03)
-
- Syntheses of myo-inositol-1,2,3,5- and 2,4,5,6-tetrakisphosphates, unusual inhibitors of myo-inositol-1,4,5-trisphosphae 3-kinase
-
D-myo-Inositol 1,4,5-trisphosphate [D-I(1,4,5)P3], a calcium mobilizing second messenger, is converted to D-I(1,3,4,5)P4 by D-I(1,4,5)P3-3-kinase. Efficient syntheses of I(1,2,3,5)P4 (2) and I(2,4,5,6)P4 (3), novel 3-kinase inhibitors, are reported.
- Chung, Sung-Kee,Chang, Young-Tae
-
p. 2715 - 2718
(2007/10/03)
-
- Practical divergent synthesis of all possible regioisomers of myo-inositol trisphosphates
-
The synthesis of all possible 12 regioisomers of IP3, some of which are implicated as second messengers in cellular signalling, is accomplished from myo-inositol via its tribenzoate derivatives (IBz3) as the key intermediates.
- Chung, Sung-Kee,Chang, Young-Tae,Sohn, Kwang-Hoon
-
p. 163 - 164
(2007/10/03)
-
- Lewis acid-catalysed rearrangement of myo-inositol orthoformate derivatives
-
Reduction of 2,4,6-tri-O-benzyl-DL-myo-inositol 1,3,5-orthoformate (1) with di-isobutylaluminium hydride gave 2,4,6-tri-O-benzyl-1,3-O-methylene-DL-myo-inositol (2), whereas reaction with trimethylaluminium gave 2,4,6-tri-O-benzyl-1,5-O-ethylidene-DL-myo-
- Gilbert, Ian H.,Holmes, Andrew B.,Pestchanker, Mauricio J.,Young, Rodney C.
-
p. 117 - 130
(2007/10/02)
-
- STUDIES ON ORGANOPHOSPHORUS COMPOUNDS 58. SYNTHESIS OF myo-INOSITOL-1,3,5-O-PHOSPHATE AS A NEW TYPE OF CAGE-PHOSPHATE
-
A new type of a cage-phosphate with resemblance to the adamantane structure namely myo-inositol-1,2,5-O-phosphate was synthesized by debenzylation of 2,4,6-O-tribenzyl-myo-inositol-1,3,5-O-phosphate, which was obtained either by direct phosphorylation of
- Yuan, Chengye,Zhai, Haixiao,Li, Yubao,Wang, Sanshan
-
-
- Total synthesis of new 1,5-bissubstituted myo-inositol derivatives. Synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and of rac. 1,5-Bissulphated and 1,5-bissulphamoylated isosteric analogues
-
Convenient synthesis of D-myo-inositol 1,5-bisphosphate, 3,5-bisphosphate and isosteric rac. 1,5-bissulphate and 1,5-bissulphonamide was accomplished from key intermediate 2,3,4,6-tetra-O-benzyl-myo-inositol.
- Westerduin, Pieter,Willems, Henrica A. M.,Van Boeckel, Constant A. A.
-
p. 6915 - 6918
(2007/10/02)
-
- Myo-inositol orthoformates
-
This invention provides the 4-mono-anion of myo-inositol orthoformate, and describes a process for preparing this anion as well as the use of this anion in the preparation of a variety of mono- and poly-phosphate derivatives of myo-inositol.
- -
-
-
- The Total Synthesis of myo-Inositol Phosphates via myo-Inositol Orthoformate
-
Novel selective alkylations of myo-inositol orthoformate (4) have been used to prepare a series of protected myo-inositol derivatives, (5a-e), (7), (10), (12), and (16).These intermediates have been used in efficient total syntheses of myo-inositol 2-phosphate, (9); myo-inositol 4-phosphate, (6); myo-inositol 1,3-bisphosphate, (18); and myo-inositol 1,3,4,5-tetrakisphosphate (14).This report represents the first total synthesis of the important natural metabolites (14) and (18) and significantly improved methods of preparation of (6) and (9).
- Billington, David C.,Baker, Raymond,Kulagowski, Janusz J.,Mawer, Ian M.,Vacca, Joseph P.,et al.
-
p. 1423 - 1429
(2007/10/02)
-
- Synthesis of myo-Inositol 1,3,4,5-Tetraphosphate and myo-Inositol 1,3-Biphosphate
-
myo-Inositol 1,3,4,5-tetraphosphate, myo-inositol 3,4-biphosphate, and myo-inositol 4-phosphate have been prepared via routes in which a key step is a novel, highly regioselective monooalkylation of myo-inositol orthoformate.
- Billington, David C.,Baker, Raymond
-
p. 1011 - 1013
(2007/10/02)
-