134680-55-0Relevant academic research and scientific papers
Construction of the octose 8-phosphate intermediate in lincomycin A biosynthesis: Characterization of the reactions catalyzed by LmbR and LmbN
Sasaki, Eita,Lin, Chia-I,Lin, Ke-Yi,Liu, Hung-Wen
, p. 17432 - 17435 (2013/01/15)
Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C 8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of d-erythro-d-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using d-fructose 6-phosphate or d-sedoheptulose 7-phosphate as the C3 donor and d-ribose 5-phosphate as the C5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C8 backbone of MTL.
Synthesis of (6,6′)-C-linked pseudodisaccharides
Mukherjee, Chinmoy,Misra, Anup Kumar
experimental part, p. 475 - 482 (2011/06/21)
A series of (6,6′)-C-linked pseudodisaccharides has been prepared using a general synthetic strategy of olefin metathesis in the presence of Grubbs second-generation catalyst. Yields were excellent in every case.
RCAI-61, the 6′-O-methylated analog of KRN7000: its synthesis and potent bioactivity for mouse lymphocytes to produce interferon-γ in vivo
Tashiro, Takuya,Nakagawa, Ryusuke,Inoue, Sayo,Shiozaki, Masao,Watarai, Hiroshi,Taniguchi, Masaru,Mori, Kenji
scheme or table, p. 6827 - 6830 (2009/04/14)
RCAI-61, the 6′-O-methylated analog of KRN7000, and six other analogs with modified 6′-position of the galactose moiety of KRN7000 were synthesized to examine their bioactivity for mouse lymphocytes. Methyl α-d-galactopyranoside was the starting material
An approach to the synthesis of α-(1-6)-C-disaccharides by tandem Tebbe methylenation and Claisen rearrangement
Chambers, David J.,Evans, Graham R.,Fairbanks, Antony J.
, p. 7184 - 7192 (2007/10/03)
Uronic acids, most efficiently synthesised from the corresponding alcohols by two step Dess-Martin and sodium chlorite mediated oxidation, may be used as coupling partners for esterification with an allo glycal as substrates for the tandem Tebbe/Claisen a
Novel synthesis of enantiomerically pure natural inositols and their diastereoisomers
Takahashi,Kittaka,Ikegami
, p. 2705 - 2716 (2007/10/03)
The various inositol polyphosphates have been found to trigger many important biological processes. Although the knowledge of this phosphoinositide signaling system has been discovered in the past 10 years, many factors remain unclear. For this reason, there is an increased demand for supplies of D-myo-inositol and particularly of novel analogues to investigate these biological mechanisms in more detail. Herein, we report the efficient syntheses of all diastereoisomers of inositol starting with 6-O-acetyl-5-enopyranosides. Conversion of 6-O-acetyl-5-enopyranosides into the corresponding substituted cyclohexanones (Ferrier-II rearrangement) was found to proceed efficiently with a catalytic amount of palladium dichloride. Stereoselective reduction of β-hydroxy ketones obtained provided the precursors to all inositol diastereoisomers in good to excellent yields and with high stereoselectivities. Good accessibility of these enantiomerically pure inositol diastereoisomers results in the efficient syntheses of D-myo-inositol 1,4,5-trisphosphate and D-myo-inositol 1,3,4,5-tetrakisphosphate.
An olefin metathesis route for the preparation of (1 → 6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis
Postema, Maarten H. D.,Calimente, Daniel,Liu, Lei,Behrmann, Tonja L.
, p. 6061 - 6068 (2007/10/03)
A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-1 in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.
Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis
Postema, Maarten H. D.,Calimente, Daniel
, p. 4755 - 4759 (2007/10/03)
The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-1,2-dideoxy-D- arabino-hex-1-enitol (5a) with a variety of sugar based carboxylic acids 6a- d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d a
A concise route to enantiomerically pure 2-arylcyclohexenones of relevance to the pancratistatin problem
Park, Tae Kyo,Danishefsky, Samuel J.
, p. 195 - 196 (2007/10/02)
A transformation involving a 6-aryl 'exo' glycal is used to prepare the target structures from carbohydrate starting materials.
Total syntheses of glucosidase inhibitors, cyclophellitols
Tatsuta, Kuniaki,Niwata, Yoshihisa,Umezawa, Kazuo,Toshima, Kazunobu,Nakata, Masaya
, p. 189 - 204 (2007/10/02)
A β-D-glucosidase inhibitor, cyclophellitol heptane-2,3,4-triol, 1> and its epoxide diastereomer, 1,6-epicyclophellitol (2) have been synthesized by using an intramolecular -cycloaddition of a n
