112612-45-0Relevant articles and documents
Synthesis and biological evaluation of enantiomeric rhamnose analogues of the antitumour agent spicamycin - Is the mode of action by modification of N-linked glycoproteins?
Martin, Angeles,Butters, Terry D.,Fleet, George W. J.
, p. 2343 - 2360 (1999)
The synthesis of both enantiomers of dodecyl rhamnospicamycin 2a and 2b, a rhamnose analogue of the naturally occurring combinatorial library spicamycin 1, are derived from L-rhamnose and methyl α-D-mannopyranoside, respectively. The L-(+)-enantiomer 2a c
USE OF FUCOSYLATION INHIBITOR FOR PRODUCING AFUCOSYLATED ANTIBODY
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, (2021/06/26)
The present invention provides inhibitors of fucosylation during protein expression from mammalian cells. The inhibitors are derived from rhamnose and act by inhibition of GDP-mannose 4,6-dehydratase (GMD). The invention further provides methods of making
Mechanistic investigation of the radical S -adenosyl- L -methionine enzyme DesII using fluorinated analogues
Lin, Geng-Min,Choi, Sei-Hyun,Ruszczycky, Mark W.,Liu, Hung-Wen
, p. 4964 - 4967 (2015/05/05)
DesII is a radical S-adenosyl-l-methionine (SAM) enzyme that can act as a deaminase or a dehydrogenase depending on the nature of its TDP-sugar substrate. Previous work has implicated a substrate-derived, C3-centered α-hydroxyalkyl radical as a key interm
Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor
Osman, Hasnah,Larsen, David S.,Simpson, Jim
body text, p. 4092 - 4098 (2009/09/30)
1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose (11) was synthesised from thiophenyl α-d-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-α-d-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and subsequent protecting group manipulation gave d-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected d-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright
Tetrazoles of manno- and rhamno- furanoses
Davis, Benjamin G.,Nash, Robert J.,Watson, Alison A.,Smith, Colin,Fleet, George W. J.
, p. 4501 - 4520 (2007/10/03)
The synthesis of [3.3.0] bicyclic tetrazoles derived from D-manno and D- rhamnofuranose staffing from D-mannose, and of L-rhamnofuranose starting from L-rhamnose is described. The key step in the formation of all three examples of this novel class of sugar mimics is an intramolecular [1,3]dipolar cycloaddition of azide and nitrile moieties.
Triterpenoid saponins from Becium grandiflorum var. obovatum
Burger, Irmgard,Burger, Barend V.,Albrecht, Carl F.,Spies, Hendrik S. C.,Sandor, Peter
, p. 2087 - 2095 (2007/10/03)
Two new triterpenoid saponins, beciumecine 1 and 2, were isolated from the root bark of Becium grandiflorum var. obovatum and their structures established as 3-O-(β-D-glucopyranosyl) terminolic acid 28-O-β-D- apiofuranosyl(1-3)-[α-L-rhamnopyranosyl(1-3)-β-D-xylopyranosyl(1-4)]-α-L- rhamnopyranosyl(1-2)-α-L-arabinopyranoside and 3-O-(β-D-glucopyranosyl) 24- hydroxyterminolic acid 28-O-α-L-rhamnopyranosyl(1-3)-β-D-xylopyranosyl(1- 4)-α-L-rhamnopyranosyl(1-2)-α-L-arabinopyranoside, respectively.
Tetrazoles of manno- and rhamno-furanoses
Davis, Benjamin,Brandstetter, Tilmann W.,Smith, Colin,Hackett, Lucy,Winchester, Bryan G.,Fleet, George W. J.
, p. 7507 - 7510 (2007/10/02)
The synthesis of tetrazoles derived from D-mannofuranose and both enantiomers of rhamnofuranose provides the first examples of tetrazole analogues of carbohydrates in the furanose form. The D-furanotetrazoles are potential mannosidase inhibitors whereas the L-rhamnotetrazole may interfere with the biosynthesis of cell walls of mycobacteria and provide a strategy for the treatment of tuberculosis and leprosy.