201670-51-1Relevant academic research and scientific papers
N-GLYCOSYLATION OF PEPTIDES AND PROTEINS
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Page/Page column 18; 19, (2015/05/05)
A process for the production of a glycoconjugate by N-glycosylation of a protein or peptide comprising the sequence D/E-X-N-X-S/T, wherein each X is the same or different and is any natural amino acid other than proline, wherein the process comprises reacting the protein or peptide with a polyisoprenyl pyrophosphate of formula (I), or a salt thereof, in the presence of PglB: (I) to produce the glycoconjugate comprising the protein or peptide having a saccharide [SI] linked to the asparagine in the sequence D/E-X-N-X-S/T. Polyisoprenylpyrophosphates used as substrates in the biocatalytic process are also provided, as well as certain glycoconjugates.
Rationally designed short polyisoprenol-linked PglB substrates for engineered polypeptide and protein N-glycosylation
Liu, Feng,Vijayakrishnan, Balakumar,Faridmoayer, Amirreza,Taylor, Thomas A.,Parsons, Thomas B.,Bernardes, Goncalo J.L.,Kowarik, Michael,Davis, Benjamin G.
, p. 566 - 569 (2014/02/14)
The lipid carrier specificity of the protein N-glycosylation enzyme C. jejuni PglB was tested using a logical, synthetic array of natural and unnatural C10, C20, C30, and C40 polyisoprenol sugar pyrophosphates, including those bearing repeating cis-prenyl units. Unusual, short, synthetically accessible C20 prenols (nerylnerol 1d and geranylnerol 1e) were shown to be effective lipid carriers for PglB sugar substrates. Kinetic analyses for PglB revealed clear KM-only modulation with lipid chain length, thereby implicating successful in vitro application at appropriate concentrations. This was confirmed by optimized, efficient in vitro synthesis allowing >90% of Asn-linked β-N-GlcNAc-ylated peptide and proteins. This reveals a simple, flexible biocatalytic method for glycoconjugate synthesis using PglB N-glycosylation machinery and varied chemically synthesized glycosylation donor precursors.
Synthesis of moenocinol and its analogs using BT-sulfone in Julia-Kocienski olefination
Huang, Hung-Jyun,Yang, Wen-Bin
, p. 1429 - 1433 (2008/02/02)
Moenocinol (C25H42O), the acyclic terpenoid unsaturated lipid part of moenomycin antibiotics, was prepared by an expedient method, which comprised organometallic reaction, Julia-Kocienski olefination, and enolate carbon bond formation as the key steps. The starting materials, nerol and 3-butyn-1-ol, were elaborated to the benzothiazole sulfone 2 and aldehyde 3, and the subsequent Julia-Kocienski olefination occurred in a stereospecific manner to give the desired 6E-configuration of moenocinol. Moenocinol (1) was thus synthesized by 10 linear steps in 12% overall yield, and its analogs 23, 24, and 28 with different chain lengths and unsaturation degrees were also realized by the similar reaction sequences.
Synthesis of tricyclopolyprenols via a radical addition and a stereoselective elimination, part II: (Z)-tricyclopentaprenol, (E,E)- and (Z,Z)-tricyclohexaprenol, (Z,Z,Z)-tricycloheptaprenol
Jenn, Thierry,Heissler, Denis
, p. 107 - 118 (2007/10/03)
Four tricyclopolyprenols have been synthesised by addition of the isocopalenyl radical either to a 2-methylene-3-hydroxy alkenenitrile (in the case of (E,E)-tricyclohexaprenol) or to a methyl 2-methylene-3-hydroxy alkenoate (in the case of the three (Z)-t
Farnesyl-diphosphate synthase. Catalysis of an intramolecular prenyl transfer with bisubstrate analogs
Jo Davisson,Neal, Timothy R.,Dale Poulter
, p. 1235 - 1245 (2007/10/02)
Bisubstrate analogs for isopentenyl diphosphate and dimethylallyl diphosphate were examined as substrates for farnesyl-diphosphate synthase. The hydrocarbon moieties of the normal substrates were joined by a one-carbon bridge that permits reaction between
