- Solid phase synthesis of muramyl dipeptides on isomeric trialkoxybenzylamine resins
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New isomeric trialkoxybenzylamine resins are developed coupling phthalimidomethyl-3,5-dimethoxyphenols to the Merrifield resin, followed by subsequent treatment with hydrazine. The generated benzylamine function allows DCC coupling with the carboxyl funct
- Kohlbau, Hans-Jürgen,Tschakert, Jochen,Al-Qawasmeh, Raed A.,Nizami, Tanveer Ahmad,Malik, Abdul,Voelter, Wolfgang
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Read Online
- Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity
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A series of muramyl dipeptide (MDP) analogues with structural modifications at the C4 position of MurNAc and on the d-iso-glutamine (isoGln) residue of the peptide part were synthesized. The C4-diversification of MurNAc was conveniently achieved by using CuAAC click strategy to conjugate an azido muramyl dipeptide precursor with structurally diverse alkynes. d-Glutamic acid (Glu), replaced with isoGln, was applied for the structural diversity through esterification or amidation of the carboxylic acid. In total, 26 MDP analogues were synthesized and bio-evaluated for the study of human NOD2 stimulation activity in the innate immune response. Interestingly, MDP derivatives with an ester moiety are found to be more potent than reference compound MDP itself or MDP analogues containing an amide moiety. Among the varied lengths of the alkyl chain in ester derivatives, the MDP analogue bearing the d-glutamate dodecyl (C12) ester moiety showed the best NOD2 stimulation potency.
- Cheng, Wei-Chieh,You, Ting-Yun,Teo, Zhen-Zhuo,Sayyad, Ashik A.,Maharana, Jitendra,Guo, Chih-Wei,Liang, Pi-Hui,Lin, Chung-Shun,Meng, Fan-Chun
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p. 3836 - 3844
(2020/10/21)
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- SYNTHETIC INNATE IMMUNE RECEPTOR LIGANDS AND USES THEREOF
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An adjuvant formulation includes a monophosphoryl Lipid A (MPLA) analogue, a Pam3CSK4 analogue, or a muramyldipeptide (MDP) analogue, or combinations thereof. The adjuvant may be formulated in soluble form or in a nanoparticle, such as polylactic glycolic acid nanoparticles. A vaccine formulation comprises the adjuvant formulation and an immunogen. Methods of vaccinating an animal include delivering the vaccine formulation to the animal.
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Paragraph 0057
(2020/06/10)
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- NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF
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The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof; wherein R1 and R2 both are hydrogen; or R1 is hydrogen and R2 is alkyl or aryl; or R1 is alkyl or aryl and R2 is hydrogen; or R1 and R2 both are alkyl or aryl (same or different groups); wherein alkyl group constitute C1-C6 alkyl or higher (both linear and branched) with or without heteroatoms; and aryl group constitute phenyl, substituted phenyl, heteraryl, arylalkyl and polynuclear aromatics. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.
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- NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF
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The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof. R = alkyl (both linear and branched), aryl, substituted aryl, alkoxy alkyl Wherein, R can be both linear and branched alkyl, aryl, substituted aryl and alkoxy alkyl. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.
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- Total Synthesis of Dansylated Park's Nucleotide for High-Throughput MraY Assays
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The membrane protein translocase I (MraY) is a key enzyme in bacterial peptidoglycan biosynthesis. It is therefore frequently discussed as a target for the development of novel antibiotics. The screening of compound libraries for the identification of MraY inhibitors is enabled by an established fluorescence-based MraY assay. However, this assay requires a dansylated derivative of the bacterial biosynthetic intermediate Park's nucleotide as the MraY substrate. Isolation of Park's nucleotide from bacteria and subsequent dansylation only furnishes limited amounts of this substrate, thus hampering the high-throughput screening for MraY inhibitors. Accordingly, the efficient provision of dansylated Park's nucleotide is a major bottleneck in the exploration of this promising drug target. In this work, we present the first total synthesis of dansylated Park's nucleotide, affording an unprecedented amount of the target compound for high-throughput MraY assays.
- Wohnig, Stephanie,Spork, Anatol P.,Koppermann, Stefan,Mieskes, Gottfried,Gisch, Nicolas,Jahn, Reinhard,Ducho, Christian
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p. 17813 - 17819
(2016/11/28)
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- Synthesis of orthogonally protected muramic acid building blocks for solid phase peptide synthesis
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Muramic acid is found in many peptide natural products containing oligo(poly)saccharide moieties. Taking into consideration that the Fmoc methodology is routinely used for solid-phase peptide synthesis, preparation of orthogonally protected muramic acid building blocks for total solid-phase synthesis of these natural products is of particular practical importance. Herein a simple and efficient synthesis of benzyl 2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-N-9-fluorenylmethyloxycarbonyl-α-D-glucopyranoside (6) from N-acetylglucosamine (1) is described. Important improvements over previous synthetic approaches to glucopyranosides 2 (benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside) and 3 (benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside), key building blocks in preparation of 6, include synthesis simplification and efficient isolation and purification. Optically pure (S)-2-chloropropionic acid 7 was prepared and introduced to the positon 3-O of sugar moiety to give compound 4 (benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside) with the (R)-configuration of the lactyl side-chain in excellent overall yield and optical purity. Deacetylation of amino group gave compound 5 (benzyl 2-amino-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α- D-glucopyranoside) suitable for incorporation of the Fmoc protecting group to give protected muramic acid derivative 6, a useful building block in peptide synthesis.
- Vlahoviek-Kahlina, Kristina,Jakas, Andreja
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p. 151 - 157
(2015/08/06)
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- Inhibitors for bacterial cell-wall recycling
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Gram-negative bacteria have evolved an elaborate process for the recycling of their cell wall, which is initiated in the periplasmic space by the action of lytic transglycosylases. The product of this reaction, β-d-N- acetylglucosamine-(1a?'4)-1,6-anhydro-β-d-N-acetylmuramyl-l- Ala-I-d-Glu-meso-DAP-d-Ala-d-Ala (compound 1), is internalized to begin the recycling events within the cytoplasm. The first step in the cytoplasmic recycling is catalyzed by the NagZ glycosylase, which cleaves in a hydrolytic reaction the N-acetylglucosamine glycosidic bond of metabolite 1. The reactions catalyzed by both the lytic glycosylases and NagZ are believed to involve oxocarbenium transition species. We describe herein the synthesis and evaluation of four iminosaccharides as possible mimetics of the oxocarbenium species, and we disclose one as a potent (compound 3, Ki = 300 A± 15 nM) competitive inhibitor of NagZ.
- Yamaguchi, Takao,Blazquez, Blas,Hesek, Dusan,Lee, Mijoon,Llarrull, Leticia I.,Boggess, Bill,Oliver, Allen G.,Fisher, Jed F.,Mobashery, Shahriar
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p. 238 - 242
(2012/05/04)
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- Synthesis of modified peptidoglycan precursor analogues for the inhibition of glycosyltransferase
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The peptidoglycan glycosyltransferases (GTs) are essential enzymes that catalyze the polymerization of glycan chains of the bacterial cell wall from lipid II and thus constitute a validated antibacterial target. Their enzymatic cavity is composed of a donor site for the growing glycan chain (where the inhibitor moenomycin binds) and an acceptor site for lipid II substrate. In order to find lead inhibitors able to fill this large active site, we have synthesized a series of substrate analogues of lipid I and lipid II with variations in the lipid, the pyrophosphate, and the peptide moieties and evaluated their biological effect on the GT activity of E. coli PBP1b and their antibacterial potential. We found several compounds able to inhibit the GT activity in vitro and cause growth defect in Bacillus subtilis. The more active was C16-phosphoglycerate-MurNAc-(l-Ala-d-Glu)-GlcNAc, which also showed antibacterial activity. These molecules are promising leads for the design of new antibacterial GT inhibitors.
- Dumbre, Shrinivas,Derouaux, Adeline,Lescrinier, Eveline,Piette, Andre,Joris, Bernard,Terrak, Mohammed,Herdewijn, Piet
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p. 9343 - 9351
(2012/07/14)
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- Phosphoramidates of monosaccharides
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The present invention relates novel phosphoramidates of monosaccharides of formula (I), wherein R1 is a monosaccharide group selected from A and B; R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and X are as defined herein. Preferably X is -O-. The present invention also provides processes for the production of compounds of formula (I), pharmaceutical compositions comprising these compounds, as well as to the use thereof in medical therapy, preferably in the treatment of osteoarthritis. wherein: R1 is selected from A and B,
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Page/Page column 29
(2012/07/14)
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- Novel phosphoramidate prodrugs of N-acetyl-(d)-glucosamine with antidegenerative activity on bovine and human cartilage explants
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(d)-Glucosamine and other nutritional supplements have emerged as safe alternative therapies for osteoarthritis (OA), a chronic and degenerative articular joint disease. In our preceding paper, a series of novel O-6 phosphate N-acetyl (d)-glucosamine prod
- Serpi, Michaela,Bibbo, Rita,Rat, Stephanie,Roberts, Helen,Hughes, Claire,Caterson, Bruce,Alcaraz, María José,Gibert, Anna Torrent,Verson, Carlos Raul Alaez,McGuigan, Christopher
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supporting information; experimental part
p. 4629 - 4639
(2012/07/01)
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- Synthesis of 1,2-cis- and 1,2-trans-glycosides of 2-acetamido-4,6-O- benzylidene-2-deoxy-d-glucopyranose by anomeric O-alkylation
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The reaction of a partially protected 1-hydroxy derivative of N-acetyl-d-glucosamine with benzyl bromide under conditions of anomeric O-alkylation was studied. It was found that the stereoselectivity of the reaction depended on the nature of the alkali me
- Pertel, Sergey S.,Gorkunenko, Oksana A.,Kakayan, Elena S.,Chirva, Vasily Ja.
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p. 685 - 688
(2011/04/26)
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- Synthesis of novel carbohydrate-based chiral P, N ligands and their applications in Cu-catalyzed enantioselective 1, 4-conjugate additions
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A new type of phosphate-pyridine (P, N) ligand derived from d-glucosamine and BINOL was synthesized and successfully applied in Cu-catalyzed enantioselective conjugate addition of diethylzinc to chalcones for the first time, high yields and enantioselectivities were obtained when the ligand 10a which contains (S)-BINOL was used. The results also showed that the configuration of BINOL at the ligand backbone had remarkable effects on the activities and enantioselectivities.
- Xia, Haijun,Yan, Hua,Shen, Chao,Shen, Fangyi,Zhang, Pengfei
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scheme or table
p. 155 - 158
(2012/03/08)
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- Design and synthesis of unnatural heparosan and chondroitin building blocks
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Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted
- Bera, Smritilekha,Linhardt, Robert J.
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scheme or table
p. 3181 - 3193
(2011/06/24)
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- Sulfonylation-induced N-to O -Acetyl migration in 2-acetamidoethanol derivatives
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The first example of sulfonylation-induced N- to O-acetyl migration of 2-acetamidoethanol derivatives is described. This type of reaction could happen with any 2-acetamidoethanol derivatives under typical sulfonylation conditions (TsCl or MsCl, pyridine) and might be a common side reaction of significance. Furthermore, the results reveal that 2-acetamidoethanol derivatives with a sterically encumbered hydroxyl group result in the migration products in high yields. The mechanism of the migration reaction is discussed.
- Yamaguchi, Takao,Hesek, Dusan,Lee, Mijoon,Oliver, Allen G.,Mobashery, Shahriar
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supporting information; experimental part
p. 3515 - 3517
(2010/08/03)
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- Hydrogen bonds as structural directive towards unusual polynuclear complexes: synthesis, structure, and magnetic properties of copper(II) and nickel(II) complexes with a 2-aminoglucose ligand
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The reaction of benzyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D- glucopyranoside (HL) with the metal salts Cu(ClO4) 2·6H2O and Ni-(NO3)2· 6H2O affords via self-assembly a tetranuclear μ4- hydroxido bridged copper(II) complex [(μ4-OH)Cu 4(L)4-(MeOH)3(H2O)](ClO 4)3 (1) and a trinuclear alcoholate bridged nickel(II) complex [Ni3(L)5(HL)]NO3 (2), respectively. Both complexes crystallize in the acentric space group P21. The X-ray crystal structure reveals the rare (μ4-OH)Cu4O 4 core for complex 1 which is μ2-alcoholate bridged. The copper(II) ions possess a distorted square-pyramidal geometry with an [NO4] donor set. The core is stabilized by hydrogen bonding between the coordinating amino group of the glucose backbone and the benzylidene protected oxygen atom O4 of a neighboring {Cu(L)} fragment as hydrogen-bond acceptor. For complex 2 an [N4O2] donor set is observed at the nickel(II) ions with a distorted octahedral geometry. The trinuclear isosceles Ni3 core is bridged by μ3-alcoholate O3 oxygen atoms of two glucose ligands. The two short edges are capped by μ2-alcoholate O3 oxygen atoms of the two ligands coordinated at the nickel(II) ion at the vertex of these two edges. Along the elongated edge of the triangle a strong hydrogen bond (244 pm) between the O3 oxygen atoms of ligands coordinating at the two relevant nickel(II) ions is observed. The coordinating amino groups of the these two glucose ligands are involved in additional hydrogen bonds with O4 oxygen atoms of adjacent ligands further stabilizing the trinuclear core. The carbohydrate backbones in all cases adopt the stable 4C1 chair conformation and exhibit the rare chitosan-like trans-2,3-chelation. Temperature dependent magnetic measurements indicate an overall antiferromagnetic behavior for complex 1 with J1 = -260 and J2 = -205 cm-1 (g = 2.122). Compound 2 is the first ferromagnetically coupled trinuclear nickel(II) complex with JA = 16.4 and JB = 11.0 cm-1 (g1,2 = 2.183, g3 = 2.247). For the high-spin nickel(II) centers a zero-field splitting of D1,2 = 3.7 cm-1 and D3 = 1.8 cm-1 is observed. The S = 3 ground state of complex 2 is consistent with magnetization measurements at low temperatures.
- Burkhardt, Anja,Spielberg, Eike T.,Simon, Sascha,Goerls, Helmar,Buchholz, Axel,Plass, Winfried
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scheme or table
p. 1261 - 1271
(2009/08/14)
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- Chemical synthesis of UDP-Glc-2,3-diNAcA, a key intermediate in cell surface polysaccharide biosynthesis in the human respiratory pathogens B. pertussis and P. aeruginosa
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In connection with studies on lipopolysaccharide biosynthesis in respiratory pathogens we had a need to access potential biosynthetic intermediate sugar nucleotides. Herein we report the chemical synthesis of uridine 5′-diphospho 2,3-diacetamido-2,3-dideoxy-α-D-glucuronic acid (UDP-Glc-2,3-diNAcA) (1) from N-acetyl-D-glucosamine in 17 steps and ~9% overall yield. This compound has proved invaluable in the elucidation of biosynthetic pathways leading to the formation of 2,3-diacetamido-2,3-dideoxy-D- mannuronic acid-containing polysaccharides. The Royal Society of Chemistry 2009.
- Rejzek, Martin,Kannathasan, Velupillai Sri,Wing, Corin,Preston, Andrew,Westman, Erin L.,Lam, Joseph S.,Naismith, James H.,Maskell, Duncan J.,Field, Robert A.
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supporting information; experimental part
p. 1203 - 1210
(2009/05/30)
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- Synthesis of protected hydroxyethylamine transition-state analogs of N-Ac-muramyl-L-alanine
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A novel N-acetyl-α-D-glucosamine derivative containing an epoxide moiety 5 has been synthesized and converted into a series of protected hydroxyethylamine transition-state analogs of N-Ac-muramyl-L-ala peptide 6a-e using a microwave-accelerated reaction. Copyright Taylor & Francis Group, LLC.
- Babic, Andrej,Pecar, Slavko
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p. 3052 - 3061
(2008/12/23)
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- Total synthesis of uridine diphosphate-N-acetylmuramoyl-l-alanine
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The first total synthesis of uridine diphosphate N-acetylmuramoyl-l-alanine in 13% overall yield is presented. The 11-step synthetic route is based on the synthetic strategy used for the synthesis of uridine diphosphate N-acetylmuramic acid, the MurC ligase substrate. However, an unexpected amide bond cleavage under basic conditions demanded crucial modifications of the final synthetic steps. The total chemical synthesis of MurD ligase substrate provides an excellent alternative to chemoenzymatic synthesis.
- Babic, Andrej,Pecar, Slavko
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experimental part
p. 2265 - 2271
(2009/04/11)
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- Optimization of UDP-N-acetylmuramic acid synthesis
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UDP-N-acetylmuramic acid (UDP-MurNAc) is a substrate of MurC, an important enzyme in the intracellular pathway of bacterial peptidoglycan biosynthesis. Various approaches towards preparation of UDP-Mur/VAc have been published but these synthetic preparations were shown to include many problematic steps. An optimization study with the focus on muramyl phosphate and UMP-morpholidate coupling was performed, resulting in a synthetic procedure enabling robust and easily reproducible production on a multi-gram scale.
- Humljan, Jan,Starcevic,Car,Stefanic Anderluh,Kocjan,Jenko,Urleb
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p. 102 - 106
(2008/09/21)
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- Synthesis of anomerically pure, furanose-free α-benzyl-2-amino-2- deoxy-D-altro- and D-manno-pyranosides and some of their derivatives
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The anomerically pure benzyl α-d-glycoside of 2-amino-2-deoxy- mannopyranoside was synthesized from d-glucopyranose via 2-amino-2-deoxy-d- altrose intermediates. Unlike the direct synthesis from mannosamine in the literature, our method provides furanose-
- Chiu, Tony M. K.,Sigillo, Katina,Gross, Paul H.,Franz, Andreas H.
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p. 2355 - 2381
(2008/02/10)
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- An improved total synthesis of UDP-N-acetyl-muramic acid
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Biochemical testing for novel inhibitors of Mur ligases requires several commercially unavailable and structurally complex substrates. We describe a modified synthetic strategy for the total chemical synthesis of the MurC ligase substrate UDP-N-acetyl-muramic acid which includes several improvements over published methods, especially with regard to purification procedures. The synthetic strategy is applicable for the synthesis of further Mur ligase substrates.
- Babi?, Andrej,Pe?ar, Slavko
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p. 4403 - 4405
(2008/02/03)
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- Synthesis of peptidoglycan units with UDP at the anomeric position
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A series of UDP-disaccharide peptide compounds were synthesized as synthetic substrate analogues or potential inhibitors of glycosyl transferase. Fluorescent compounds have been prepared with the aim of developing a screening method for selecting transglycosylase inhibitors.
- Lioux, Thierry,Busson, Roger,Rozenski, Jef,Nguyen-Disteche, Martine,Frere, Jean-Marie,Herdewijn, Piet
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p. 1615 - 1641
(2007/10/03)
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- Fluorinated glucosamine analogs useful for modulating post-translational glycosylations on cells
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The present invention provides compositions and methods for inhibiting cell migration, e.g., lymphocytes and inflammation. The invention also provides an improved process for preparing fluorinated N-acetylglucosamines.
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- One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi
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Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O- benzoyl-2-deoxy-α-D-glucopyranoside (4) with penta-O-benzoyl-β-D- galactopyranose (6) gave the derivative of β-D-Galp-(1 → 6)-α-D-GlcNAc 7 in 80% yield. This was glycosylated with penta-O-benzoyl-α,β-D- galactofuranose (5), employing the same catalyst, to afford the protected benzyl per-O-benzoyl-β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]D-GlcNAc 10 in 41% yield. Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). β-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide β-D-Galf(1 → 4)[ β-D-Galp(l → 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi.
- Gallo-Rodriguez, Carola,Varela, Oscar,De Lederkremer, Rosa M.
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p. 163 - 170
(2007/10/03)
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- Probing the Acceptor Specificity of β-1,4-Galactosyltransferase for the Development of Enzymatic Synthesis of Novel Oligosaccharides
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β-1,4-Galactosyltransferase has been investigated with regard to its acceptor specificity and used in the synthesis of galactosides with 5-thioglucose, glucal, deoxynojirimycin, modified N-acetylglucosamine, and glucose derivatives as acceptors. The galactoside products are potentially useful as endoglycosidase or glycosyltransferase inhibitors or as intermediates for the synthesis of complex oligosaccharides. The conformation of each enzyme product has been investigated with NMR; all arc shown to possess similar glycosidic torsional angles based on a significant NOE between H-1 of Gal and H-4 of the acceptor. Comparison of the transferase reactions with the β-1,4-galactosidase-catalyzed galactosyl transfer reactions indicates that the transferase reactions provide exclusively a β-1,4-glycosidic linkage while the galactosidase reactions predominantly form a β-1,6-glycosidic linkage.
- Wong, Chi-Huey,Ichikawa, Yoshitaka,Krach, Thomas,Narvor, Christine Gautheron-Le,Dumas, David P.,Look, Gary C.
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p. 8137 - 8145
(2007/10/02)
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- ERPROBTE SYNTHESE VON 2-AZIDO-2-DESOXY-D-MANNOSE UND 2-AZIDO-2-DESOXY-D-MANNURONSAEURE ALS BAUSTEIN ZUM AUFBAU VON BAKTERIEN-POLYSACCHARID-SEQUENZEN
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The azidonitration of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol at low temperature afforded preponderantly the azidonitrate having the D-manno configuration.After reaction with sodium acetate, 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose was directly isolated and deblocking gave 2-azido-2-deoxy-D-mannopyranose. 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide and 2-azido-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide were prepared and are suitable for selective α- and β-glycoside synthesis.In the presence of platinum-oxygen, the catalytic oxidation of benzyl 2-azido-2-deoxy-α-D-mannopyranoside gave in high yields (benzyl 2-azido-2-deoxy-α-D-mannopyranosid)uronic acid from which 2-amino-2-deoxy-D-mannopyranuronic acid was obtained.By catalytic oxidation, selectively blocked derivatives of 2-amino-2-deoxy-D-mannopyranose were converted into the correspondind uronic acid derivatives.
- Paulsen, Hans,Lorentzen, Jens Peter,Kutschker, Wolfram
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p. 153 - 176
(2007/10/02)
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- Further Aspects of the Reduction of Dithiocarbonates with Tributyltin Hydride and Deuteride
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The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio)thiocarbonyl-β-D-idose, -talose, and -(3-(2H))talose with tributyltin hydride and deuteride leads to the deoxy sugar and some deuteriumcontaining deoxy sugars.A modification of the normal procedure allows for reduction with tributyltin hydride generated in situ.As well, the reduction of some dithiocarbonates derived from glycosides of N-acetyl-D-glucosamine allows to a variety of dideoxy and trideoxy sugars.
- Conway, Richard J.,Nagel, Jennifer P.,Stick, Robert V.,Tilbrook, D. Matthew G.
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p. 939 - 945
(2007/10/02)
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