- VACCINE COMPOSITIONS AND ANTIBODIES FOR LYME DISEASE
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The present invention relates to vaccine compositions comprising lipid antigens, antibodies targeting lipid antigens, pharmaceutical compositions comprising such and their use in diagnosing, monitoring, treating, and preventing infectious disease, such as Lyme disease. In one aspect, administered is a therapeutically effective amount of a vaccine composition comprising a lipid antigen, an antibody or fragment thereof binding a lipid antigen, and/or a pharmaceutical composition comprising an antibody or fragment thereof binding a lipid antigen. Other aspects are described.
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- Experimental and theoretical study of the O3/O4 regioselectivity of glycosylation reactions of glucopyranosyl acceptors
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The knowledge of the regioselectivity between different hydroxyl groups of glycosyl acceptors is valuable in planning simple strategies for the synthesis of oligosaccharides, minimizing the use of protecting groups. With the aim of obtaining deeper knowle
- Del Vigo, Enrique A.,Stortz, Carlos A.,Marino, Carla
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- ENDOSOMAL CLEAVABLE LINKERS
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The present disclosure relates generally to cleavable linkers and uses thereof.
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Paragraph 00563
(2018/08/20)
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- The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application
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The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac
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Paragraph 0041; 0050; 0053
(2017/04/28)
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- 3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application
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The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl
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Paragraph 0035; 0039; 0059
(2017/08/25)
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- Cross metathesis assisted solid-phase synthesis of glycopeptoids
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A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yield
- Khan, Sharaf Nawaz,Kim, Arim,Grubbs, Robert H.,Kwon, Yong-Uk
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p. 2952 - 2955
(2012/07/30)
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- Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities
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In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.
- Li, Xiao-Dong,Kang, Shuai-Tao,Li, Guo-Yu,Li, Xian,Wang, Jin-Hui
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experimental part
p. 3580 - 3596
(2011/07/07)
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- Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides
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Invasive fungal infections pose a significant problem to the immune-compromised. Moreover, increased resistance to common antifungals requires development of novel compounds that can be used to treat invasive fungal infections. Naturally occurring steroid
- Cammarata, Amy,Upadhyay, Sunil Kumar,Jursic, Branko S.,Neumann, Donna M.
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supporting information; experimental part
p. 7379 - 7386
(2012/02/13)
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- Mitochondrial affinity of guanidine-rich molecular transporters built on monosaccharide scaffolds: Stereochemistry and lipophilicity
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We synthesized eight G8 molecular transporters (MTs) based on 4 different monosaccharide scaffolds, and studied their biological properties with a special focus on possible mitochondrial targeting and tissue selectivity. The mitochondrial affinity of these MTs was found to be clearly related to the scaffold stereochemistry and also tenuously with the lipophilicity. It may be suggested that in the practical delivery strategy of drugs for the brain and mitochondrial diseases the BBB permeability and mitochondrial affinity should be considered as key parameters, and that an enhanced mitochondrial affinity appears possible by further research on the structure-property relationship of guanidine-rich molecular transporters.
- Lee, Woo Sirl,Kim, Wanil,Kim, Kyong-Tai,Chung, Sung-Kee
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p. 2286 - 2300
(2012/06/16)
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- A short semi-synthesis and complete NMR-spectroscopic characterization of the naturally occurring lignan glycoside matairesinol 4,4′-di-O-β-d- diglucoside
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A convenient semi-synthesis of (8R,8′R)-matairesinol 4,4′-di-O-β-d-glucopyranoside (MDG), found in the stems of Trachelospermum asiaticum var. intermedium, is described starting from the readily available starting materials d-glucose and hydroxymatairesin
- Ekholm, Filip S.,Eklund, Patrik,Leino, Reko
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body text
p. 1963 - 1967
(2010/10/18)
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- Synthesis and properties of a photoactivatable analogue of psychosine (β-galactosylsphingosine)
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(Chemical Equation Presented) Photoaffinity probes: The first synthesis of a photoaffinity probe of psychosine (blue) is reported, where benzophenone (red) is tethered as a crosslinking moiety. This photo-psychosine probe (shown) displayed a similar potency as psychosine in stimulating Ca2+ flux in U937 cells, suggesting that it may be useful for labeling and identifying the still unidentified psychosine receptor(s) by mass spectrometry.
- Lankalapalli, Ravi S.,Baksa, Attila,Liliom, Karoly,Bittman, Robert
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experimental part
p. 682 - 686
(2011/01/05)
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- SnCl4- and TiCl4-catalyzed anomerization of acylated O - And S -glycosides: Analysis of factors that lead to higher α: β d reaction rates
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The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl4 and TiCl4 and how this has informed the synthesis of α-O- and α-S-glycolipids is discussed. The SnCl4-catalyzed anomerization reactions of β-S- and β-O-glycosides of 18 substrates followed first order equilibrium kinetics and kf + kr values were obtained, where kf is the rate constant for the forward reaction (β → α) and kr is the rate constant for the reverse reaction (α → β). Comparison of the kf + k r values showed that reactions of glucuronic acid or galacturonic acid derivatives were ~10 to 3000 times faster than those of related glucoside and galactopyranoside counterparts and α:β ratios were generally also higher. Stereoelectronic effects contributed from galacto-configured compounds were up to 2-fold faster than those of corresponding glucosides. The introduction of groups, including protecting groups, which are increasingly electron releasing generally led to rate enhancements. The anomerization of S-glycosides was consistently faster than that of corresponding O-glycosides. Reactions were generally faster for reactions with TiCl4 than those with SnCl4. Anomeric ratios depended on the Lewis acid, the number equivalents of the Lewis acid, temperature, and substrate. Very high ratios of α-products for both O- and S-glucuronides were observed for reactions promoted by TiCl4; for these substrates TiCl4 was superior to SnCl4. Anomeric ratios from anomerization of S-glucosides were higher with SnCl4 than with TiCl4. The dependence of equilibrium ratio on Lewis acid and the number of equivalents of Lewis acid indicated that the equilibrium ratio is determined by a complex of the saccharide residue bound to the Lewis acid and not the free glycoside. The high α:β ratios observed for anomerization of both O- and S-glycuronic acids can be explained by coordination of the C-1 heteroatom and C-6 carbonyl group of the product to the Lewis acid, which would enhance the anomeric effect by increasing the electron-withdrawing ability of the anomeric substituent and lead to an increase in the proportion of the α-anomer. Such an observation would argue against the existence of a reverse anomeric effect. Support for a chelation-induced endocyclic cleavage mechanism for the anomerization is provided by the trapping of a key intermediate. The data herein will help predict the tendency of β-glycosides to undergo anomerization; this includes cases where 1,2-trans glycosides are initial products of glycosidation reactions catalyzed by TiCl4 or SnCl4.
- Pilgrim, Wayne,Murphy, Paul V.
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supporting information; experimental part
p. 6747 - 6755
(2010/12/25)
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- Synthesis and cytotoxicity evaluation of natural α-bisabolol β-d-fucopyranoside and analogues
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α-Bisabolol β-d-fucopyranoside, a cytotoxic naturally occurring compound, was efficiently synthesized along with five other α-bisabolol glycosides (β-d-glucoside, β-d-galactoside, α-d-mannoside, β-d-xyloside and α-l-rhamnoside). Glycosidation of α-bisabol
- Piochon, Marianne,Legault, Jean,Gauthier, Charles,Pichette, Andre
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experimental part
p. 228 - 236
(2009/09/05)
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- Sugar/Steroid/Sugar Conjugates: Sensitivity of Lipid Binding to Sugar Structure
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(Equation presented) Three steroids, each bearing a sugar on rings A and D, have been synthesized. Their effect on the "melting" behavior of a lipid bilayer depends on whether the sugar is glucose, galactose, or mannose. Packing constraints dictate how th
- Mbadughat, Bessie N. A.,Menger, Fredric M.
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p. 4041 - 4044
(2007/10/03)
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- Syntheses and interfacial behaviour of neoglycolipid analogues of glycosyl ceramides
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Four glycosyl ceramides analogues having D-galactose or 2-acetamido-2-deoxy-D-glucose moieties linked to enantiomeric lipids have been synthesised to study their interfacial behaviour at the air | water interface. The lipid chains were prepared in two steps by opening 1,2-epoxyhexadecane using Jacobsen kinetic hydrolytic resolution (KHR) followed by an azidosilylation reaction of the diol so obtained. Glycosylation reactions were realised either with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate or 1,3,4,6-tetra-O-acetyl-2-allyloxycarbonylamino-2-deoxy-β-D-glucopyranose as donors and (2R)- or (2S)-2-azidohexadecanol derivatives as acceptors. Transformation of the azido glycosides into N-acylated products was done by a modified Staudinger reaction in the presence of fatty acyl chlorides. The four neoglycolipids are able to form a condensed monolayer at the air | water interface; their π-A isotherm diagrams are similar to that described for the natural glycosyl ceramides. The detailed analysis of the isotherms, taking into account the chirality of the lipid chains, allowed to determine the contribution of the different parts of the molecule under the monolayer packing.
- Lafont, Dominique,Bouchu, Marie-Noelle,Girard-Egrot, Agnes,Boullanger, Paul
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p. 181 - 194
(2007/10/03)
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- A simple access to 3,6-branched oligosaccharides: Synthesis of a glycopeptide derivative that relates to Lycium barbarum L.
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An efficient method is described for the synthesis of galactopyranosyl-containing 3,6-branched oligosaccharides using isopropyl thiogalactopyranoside as starting material. This method is successfully applied to the preparation of a glycopeptide derivative that relates to Lycium barbarum L. The potential application of isopropyl thioglycoside in glycosylation is also investigated.
- Du, Yuguo,Zhang, Meimei,Yang, Feng,Gu, Guofeng
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p. 3122 - 3127
(2007/10/03)
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- Parasite glycoconjugates. Part 9. Synthesis of dec-9-enyl β-D-galactopyranosyl-(1→4)-α-D-mannopyranosyl phosphate and its epimers at the D-galactose moiety, substrate analogues for the elongating α-D-mannopyranosylphosphate transferase in the Leishmania
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A set of phosphodisaccharides, substrate analogues, which will be used to study the acceptor substrate specificity of the Leishmania biosynthetic enzymes, have been synthesized using the trichloroacetimidate method for the glycosylation reactions, SN
- Ivanova, Irina A.,Ross, Andrew J.,Ferguson, Michael A. J.,Nikolaev, Andrei V.
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p. 1743 - 1753
(2007/10/03)
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- Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans
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2,3,4,6-Tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate was condensed with benzyl 2,3-O-isopropylidene-β-D-xylopyranoside to give the corresponding β-(1->4)-linked disaccharide derivative, which was transformed into 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-xylopyranosyl trichloroacetimidate.This glycosyl donor was condensed with a set of selectively C,N-protected L-seryl-glycine dipeptide units.Selective deblocking at the C- or N-termini of the glycosylated or non-glycosylated dipeptide segments, and coupling using the mixed-anhydride procedure allowed the construction in high yield of partially or fully glycosylated oligopeptides from the carbohydrate-protein linkage region of proteoglycans.
- Rio, Sandrine,Beau, Jean-Marie,Jacquinet, Jean-Claude
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