Corrigendum

Gigg, Jill; Gigg, Roy; Payne, Sheila; Conant, Robert; Barluenga, José; Martinez-Gallo, J. M.; Nájera, Carmén; Fañanás, Francisco J.; Yus, Miguel

doi:10.1039/p19880000981

Cited by 51 publications

(73 citation statements)

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“…This 'colour and hopping effect' can be observed many times on taking the same sample of this perhydropyrene stereoisomer through this heating and cooling cycle (Kohne, Praefcke & Mann, 1988). The same phenomenon is observed for a derivative of hexahydroxycyclohexane (myo-inositol; Gigg, Gigg, Payne & Conant, 1987;Steiner, Hinrichs, Saenger & Gigg, 1988), which displays this 'colour and hopping effect' at two temperatures (Kohne, Praefcke & Mann, 1988). The X-ray crystal structure of ttattperhydropyrene was determined to provide detailed information about the crystal packing pattern in the unit cell and the conformation of the molecule.…”

Section: Transtransanti Trans Trans-perhydropyrene ( Ttatt-per-mentioning

confidence: 69%

A crystal that hops in phase transition, the structure of trans,trans,anti,trans,trans-perhydropyrene

Ding¹,

Herbst²,

Praefcke³

et al. 1991

Acta Crystallogr Sect B

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Abstracttrans,trans,anti, trans,trans-Perhydropyrene, ( 1,2,3,-3ar,4,5,5at,6,7,8,8at,9,10,10ac, lographically independent molecules in the asymmetric unit are tilted with respect to each other at a dihedral angle of 53-9" the crystal structure is of a layer type with hexagonal packing. Upon heating, a phase transformation occurs at 344.5 K which is associated with jumps of the crystals almost 6 cm high. The transformation is probably of the martensitic type with lateral shifts of lattice planes relative to each other.

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Section: Transtransanti Trans Trans-perhydropyrene ( Ttatt-per-mentioning

confidence: 69%

A crystal that hops in phase transition, the structure of trans,trans,anti,trans,trans-perhydropyrene

Ding¹,

Herbst²,

Praefcke³

et al. 1991

Acta Crystallogr Sect B

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“…Likewise, an allyl aglycon was introduced as temporary anomeric protection of all intermediates. Moreover, as demonstrated decades ago and subsequently exploited in the synthesis of various bacterial oligosaccharides including SF3a, SF6, and SF1b O‐Ag substructures, the efficient Pd/C‐catalyzed hydrogenation of the allyl moiety into a propyl ether provided the targets as propyl glycosides. Furthermore, the 4 D ,6 D ‐diol was protected as an isopropylidene acetal, previously shown to avoid possible interference due to anisotropic shielding observed when using a benzylidene acetal in related contexts .…”

Section: Resultsmentioning

confidence: 97%

Detailed Investigation of the Immunodominant Role of O‐Antigen Stoichiometric O‐Acetylation as Revealed by Chemical Synthesis, Immunochemistry, Solution Conformation and STD‐NMR Spectroscopy for Shigella flexneri 3a

Boutet

Blasco

Guerreiro

et al. 2016

Chemistry A European J

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Shigella flexneri 3a causes bacillary dysentery. Its O-antigen has the {2)-[α-d-Glcp-(1→3)]-α-l-Rhap-(1→2)-α-l-Rhap-(1→3)-[Ac→2]-α-l-Rhap-(1→3)-[Ac→6]≈40 % -β-d-GlcpNAc-(1→} ([(E)ABAc CAc D]) repeating unit, and the non-O-acetylated equivalent defines S. flexneri X. Propyl hepta-, octa-, and decasaccharides sharing the (E')A'BAc CD(E)A sequence, and their non-O-acetylated analogues were synthesized from a fully protected BAc CD(E)A allyl glycoside. The stepwise introduction of orthogonally protected mono- and disaccharide imidate donors was followed by a two-step deprotection process. Monoclonal antibody binding to twenty-six S. flexneri types 3a and X di- to decasaccharides was studied by an inhibition enzyme-linked immunosorbent assay (ELISA) and STD-NMR spectroscopy. Epitope mapping revealed that the 2C -acetate dominated the recognition by monoclonal IgG and IgM antibodies and that the BAc CD segment was essential for binding. The glucosyl side chain contributed to a lesser extent, albeit increasingly with the chain length. Moreover, tr-NOESY analysis also showed interaction but did not reveal any meaningful conformational change upon antibody binding.

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“…The 1 H and 13 C NMR spectra of 10 were identical to those reported for 1-O-methyl-myo-inositol [(À)-bornesitol], [19] although the specific rotation of 10 was opposite in sign, identifying it as (+)-bornesitol (3-Omethyl-myo-inositol). [20] This identified (+ )-3 a as the 1,6:4,5-protected compound, and enabled the absolute configurations of all chiral intermediates and products to be assigned.…”

Section: Resultsmentioning

confidence: 99%

A Definitive Synthesis ofD‐myo‐Inositol 1,4,5,6‐Tetrakisphosphate and Its EnantiomerD‐myo‐Inositol 3,4,5,6‐Tetrakisphosphate from a Novel Butane‐2,3‐diacetal‐Protected Inositol

Mills¹,

Riley²,

Liu³

et al. 2003

Chemistry A European J

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New and rapid syntheses of the enantiomeric intracellular signalling molecules d-myo-inositol 1,4,5,6-tetrakisphosphate (1 a) and D-myo-inositol 3,4,5,6-tetrakisphosphate (1 b) are described. The synthetic strategy employs the novel butane-2,3-diacetal-protected (BDA-protected) myo-inositol (+/-)-3 ab, directly accessible from myo-inositol on a large scale, and an optical resolution with diastereoisomeric (R)-(-)-acetylmandelate esters. The X-ray crystal structure of (+/-)-4, an unusual side product of acid-catalysed reaction of myo-inositol with butanedione is also presented, and the absolute configurations of 1 a and 1 b are definitively assigned by conversion of key precursors into (+)-bornesitol and L-iditol hexaacetate, respectively. Biological activity of synthetic 1 b was confirmed in comparison with the natural polyphosphate.

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Corrigendum

Cited by 51 publications

References 0 publications

A crystal that hops in phase transition, the structure of trans,trans,anti,trans,trans-perhydropyrene

A crystal that hops in phase transition, the structure of trans,trans,anti,trans,trans-perhydropyrene

Detailed Investigation of the Immunodominant Role of O‐Antigen Stoichiometric O‐Acetylation as Revealed by Chemical Synthesis, Immunochemistry, Solution Conformation and STD‐NMR Spectroscopy for Shigella flexneri 3a

A Definitive Synthesis ofD‐myo‐Inositol 1,4,5,6‐Tetrakisphosphate and Its EnantiomerD‐myo‐Inositol 3,4,5,6‐Tetrakisphosphate from a Novel Butane‐2,3‐diacetal‐Protected Inositol

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