- Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides
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The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.
- Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan
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p. 1874 - 1880
(2019/07/22)
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- Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents
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The invention relates to a synthetic route of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents, and belongs to the field of synthesis of novel sweetening agents. The novel sweetening agent with higher swe
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- Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions
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A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.
- Balzer, Paul G.,Blaszczyk, Stephanie A.,Duan, Xiyan,Ma, Zhi-Xiong,Simmons, Christopher J.,Stevens, Christopher M.,Tang, Weiping,Wang, Hao-Yuan,Wen, Peng,Ye, Wenjing,Yin, Dan
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supporting information
(2020/02/28)
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- Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
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The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.
- Singh, Yashapal,Demchenko, Alexei V.
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supporting information
p. 1461 - 1465
(2019/01/04)
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- Regenerative Glycosylation
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Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.
- Singh, Yashapal,Wang, Tinghua,Geringer, Scott A.,Stine, Keith J.,Demchenko, Alexei V.
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p. 374 - 381
(2018/01/01)
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- Stereoselective Epimerizations of Glycosyl Thiols
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Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
- Doyle, Lisa M.,O'Sullivan, Shane,Di Salvo, Claudia,McKinney, Michelle,McArdle, Patrick,Murphy, Paul V.
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supporting information
p. 5802 - 5805
(2017/11/10)
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- Sites for dynamic protein-carbohydrate interactions of O- and C-linked mannosides on the E. coli FimH adhesin
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Antagonists of the Escherichia coli type-1 fimbrial adhesin FimH are recognized as attractive alternatives for antibiotic therapies and prophylaxes against acute and recurrent bacterial infections. In this study α-D-mannopyranosides O- or C-linked with an
- Touaibia, Mohamed,Krammer, Eva-Maria,Shiao, Tze C.,Yamakawa, Nao,Wang, Qingan,Glinschert, Anja,Papadopoulos, Alex,Mousavifar, Leila,Maes, Emmanuel,Oscarson, Stefan,Vergoten, Gerard,Lensink, Marc F.,Roy, René,Bouckaert, Julie
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supporting information
(2017/08/30)
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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; 0037; 0113
(2017/08/25)
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- DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO
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The present invention relates to methods for synthesizing compounds of formula I or pharmaceutically acceptable salts thereof: I wherein each of X, Alk1, Alk2, and W are as defined and described herein.
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Paragraph 0634; 0635
(2013/07/31)
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- DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO
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The present invention relates to methods for synthesizing compounds of formula I or pharmaceutically acceptable salts thereof: (I) wherein each of X, Alk, and W are as defined and described herein.
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Paragraph 0408; 0409
(2013/06/04)
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- A novel "pro-sensitizer" based sensing of enzymes using Tb(iii) luminescence in a hydrogel matrix
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Chemically synthesized "pro-sensitizers" release the sensitizer in the presence of lipase or β-glucosidase, triggering a significant luminescence response from a lanthanide based hydrogel. The Royal Society of Chemistry 2012.
- Bhowmik, Sandip,Maitra, Uday
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supporting information; experimental part
p. 4624 - 4626
(2012/06/05)
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- Glycosidation of thioglycosides in the presence of bromine: Mechanism, reactivity, and stereoselectivity
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Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, α-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into α-bromide that is totally unreactive under the established reaction conditions.
- Kaeothip, Sophon,Yasomanee, Jagodige P.,Demchenko, Alexei V.
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scheme or table
p. 291 - 299
(2012/03/08)
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- Total synthesis of the fully lipidated glycosylphosphatidylinositol (GPI) anchor of malarial parasite Plasmodium falciparum
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We report a new and convergent strategy for the total synthesis of fully lipidated glycosylphosphatidylinositol (GPI) anchor, the major pro-inflammatory factor of malarial parasite (Plasmodium falciparum). The key features of our approach include, the acc
- Ali, Asif,Vishwakarma, Ram A.
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scheme or table
p. 4357 - 4369
(2010/07/06)
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- BINDING-SITE MODIFIED LECTINS AND USES THEREOF
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In one aspect, the disclosure provides cross-linked materials that include multivalent lectins with at least two binding sites for glucose, wherein the lectins include at least one covalently linked affinity ligand which is capable of competing with gluco
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Page/Page column 95
(2010/08/09)
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- Indium(III) triflate-mediated one-step preparation of glycosyl halides from free sugars
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In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glyc
- Giri, Santosh Kumar,Kartha, K. P. Ravindranathan
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experimental part
p. 3378 - 3383
(2010/12/25)
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- A properly protected sphingosine acceptor for helferich glycosylation
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The synthesis and some examples of glycosylations of a properly protected sphingosine is presented. This compound is suitable for the preparation of glycosphingolipids. It has been used for the synthesis of -mannosylceramide and sulfatide exploiting the anchimeric assistance to address the stereochemistry of the glycosidic bond.
- Michieletti, Mario,Sillani, Laura,Panza, Luigi
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body text
p. 2609 - 2612
(2010/02/28)
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- Synthesis of a derivative of a pentasaccharide repeating unit of the O-antigenic polysaccharide of the bacterium Klebsiella pneumoniae O3 as a benzoylated 2-methoxycarbonylethyl thioglycoside
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Block synthesis of a fully benzoylated derivative of the pentasaccharide α-d-Manp-(1→3)-α-d-Manp-(1→2)-α-d-Manp-(1→2) -α-d-Manp-(1→2)-α-d-Manp-SCH2CH2CO 2Me, the glycoside of the repeating unit of the O-antigenic polysaccharide of the bacterium Klebsiella pneumoniae O3, was performed.
- Abronina,Galkin,Backinowsky,Grachev
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scheme or table
p. 457 - 467
(2010/07/08)
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- Efficient chemical synthesis of a dodecasaccharidyl lipomannan component of mycobacterial lipoarabinomannan
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(Chemical Equation Presented) Lipomannan (LM) is one of the domains of lipoarabinomannan (LAM) glycolipids, the latter being one of several cell surface organic molecules that fortify mycobacterial species against external attack. Some members of mycobacterial families are pathogenic, most notably Mycobacterium tuberculosis and Mycobacterium leprae, while others are nonpathogenic, and used in the clinic, such as Mycobacterium smegmatis. Additional biological significance arises from the fact that LM has been implicated in several health disorders outside of those associated with mycobacterial pathogens, notably for treatment of bladder cancer. LM is comprised of a heavily lipidated phosphoinositide dimannoside headgroup, from which a mannan array, of varied complexity, extends. The latter consists of a 1,6-α-linked backbone flanked at position O2, not necessarily regularly, with α-linked mannosides. This paper gives an example of lipomannan synthesis in which all of the sugar components, whether functioning as donors or acceptors, are obtained from n-pentenyl orthoesters, themselves in turn prepared in three easy steps from D-mannose. Assembly of the mannan array is facilitated by the exquisite regioselectivity occasioned by the use of ytterbium triflate/N-iodosuccinimide as the trigger for reaction of n-pentenyl orthoesters.
- Fraser-Reid, Bert,Chaudhuri, Siddharfha Ray,Jayaprakash,Lu, Jun,Ramamurty, Changalvala V. S.
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scheme or table
p. 9732 - 9743
(2009/04/06)
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- Automated synthesis of lipomannan backbone α(1-6) oligomannoside via glycosyl phosphates: Glycosyl tricyclic orthoesters revisited
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Glycosyl tricyclic orthoesters provide a versatile basis for the efficient generation of glycosyl phosphates, which are used in the automated synthesis of lipomannan backbone α(1-6) hexa-mannoside. The Royal Society of Chemistry.
- Liu, Xinyu,Wada, Reiko,Boonyarattanakalin, Siwarutt,Castagner, Bastien,Seeberger, Peter H.
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supporting information; experimental part
p. 3510 - 3512
(2009/02/05)
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- Immunogenic glycopeptides, screening, preparation and uses
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The invention relates to immunogenic glycopeptides derived from pathogenic microorganisms, which can be used for immunization and diagnosing infections dye to such pathogenic microorganisms and also to method for the selection and preparation thereof.
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Page/Page column 11; sheet 7
(2008/06/13)
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- Combinatorial synthesis of an oligosaccharide library by using β-bromoglycoside-mediated iterative glycosylation of selenoglycosides: Rapid expansion of molecular diversity with simple building blocks
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A new method for constructing an oligosaccharide library composed of structurally defined oligosaccharides is presented based on an iterative glycosylation of selenoglycosides. Treatment of 2-acyl-protected selenoglycosides with bromine selectively generates β-bromoglycosides, which serve as glycosyl cation equivalents in the oligosaccharide synthesis. Thus, the coupling of the bromoglycosides with another selenoglycoside affords the corresponding glycosylated selenoglycosides, which can be directly used to next glycosylation. The iteration of this sequence allows the synthesis of a variety of oligosaccharides including an elicitor active heptasaccharide. A characteristic feature of the iterative glycosylation is that glycosyl donors and acceptors with the same anomeric reactivity can be selectively coupled by activation of the glycosyl donor prior to coupling with the glycosyl acceptor. Therefore, same selenoglycosides can be used for both the glycosyl donors and the acceptors. This feature has been exemplified by a construction of an oligosaccharide library directed to elicitor-active oligosaccharides. The library composed of stereochemically defined oligoglucosides with considerable structural diversity can be constructed starting from simple selenoglycosides.
- Yamago, Shigeru,Yamada, Takeshi,Ito, Hiroki,Hara, Osamu,Mino, Yosuke,Yoshida, Jun-Ichi
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p. 6159 - 6174
(2007/10/03)
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- Investigation of nonspecific effects of different dyes in the screening of labeled carbohydrates against immobilized proteins
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Carbohydrates play an important role in life processes, and combinatorial chemistry can provide useful sources of thousands of synthetic carbohydrates as potential ligands for biological receptors. To accelerate the detection of positive hits arising from specific interactions between a carbohydrate and a protein, the use of fluorescent dyes can serve as a reliable detecting tool. A study of labeled carbohydrates to lectins conjugated to a solid-support shows that succinimidyl 6-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)hexanoate (NBD-X) dye provides by far the lowest level of nonspecific interaction with immobilized protein. This observation is in stark contrast with the commonly used labeling reagents constituted of charged and aromatic groups, for instance, FITC and TAMRA dyes.
- Dowlut, Meenakshi,Hall, Dennis G.,Hindsgaul, Ole
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p. 9809 - 9813
(2007/10/03)
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- Zinc triflate-benzoyl bromide: A versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides
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A simple and efficient method is developed for the chemoselective one-pot conversion of ethers (benzyl, TBDMS and acetal) to the corresponding benzoates by zinc triflate-catalyzed deprotection and benzoylation by benzoyl bromide. In the same reaction, methyl or p-methoxyphenyl glycosides are converted into glycosyl bromides that are useful in glycosylation reactions.
- Polat, Tuelay,Linhardt, Robert J.
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p. 447 - 449
(2007/10/03)
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- Comparing n-pentenyl orthoesters and n-pentenyl glycosides as alternative glycosyl donors
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As is well known, cyclic 1,2-glycosyl orthoesters undergo ready acid catalyzed rearrangement to 2-O-acyl glycosides in which the alkoxy group is transferred from the orthoester to the anomeric center in a highly stereocontrolled process. The related n-pentenyl derivatives are unique in that either the orthoester (NPOE) or its rearrangement product (NPGAC) can function as a glycosyl donor, and mechanistic considerations indicate that both should (or could!) lead to the same product(s) arising from trans-orthoesterification, glycosidation, glycosyl esterification, etc. Experiments are described which show that the product obtained from a given reaction can be optimized by careful choice of the donor, NPOE or related NPGAC, and careful attention to reaction conditions, electrophilic promoter, 'size' of the glycosyl acceptor, and experimental protocol.
- Mach, Mateusz,Schlueter, Urs,Mathew, Felix,Fraser-Reid, Bert,Hazen, Kevin C
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p. 7345 - 7354
(2007/10/03)
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- A new, iterative strategy of oligosaccharide synthesis based on highly reactive β-bromoglycosides derived from selenoglycosides
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equation presented Stereoselective conversion of a selenoglycoside to a β-bromoglycoside in the absence of a glycosyl acceptor followed by the coupling with another selenoglycoside affords the corresponding glycosylated selenoglycoside, which could be dir
- Yamago, Shigeru,Yamada, Takeshi,Hara, Osamu,Ito, Hiroki,Mino, Yosuke,Yoshida, Jun-Ichi
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p. 3867 - 3870
(2007/10/03)
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- Synthesis of aliphatic O-dimannosyl amino acid building blocks for solid-phase assembly of glycopeptide libraries
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The preparations of α(1,2)-, α(1,3)- and α(1,6)-linked mannose disaccharides is described.The protected α-D-Man(1-->3)-D-Man disaccharide was synthesized using the trichloroacetimidate method, while the Koenigs-Knorr procedure was employed in the preparation of the 1-->2- and 1-->6-linked disaccharides.Glycosylation of NΑ-Fmoc-Ser-OPfp , Nα-Fmoc-Thr-OPfp and Nα-Fmoc-Hyp-OPfp with the dimannosyl bromides afforded the activated building blocks, in moderate to high yield, for direct use in solid-phase synthesis of glycopeptide libraries.
- Franzyk, Henrik,Meldal, Morten,Paulsen, Hans,Bock, Klaus
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p. 2883 - 2898
(2007/10/02)
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- Studies related to synthesis of glycophosphatidylinositol membrane-bound protein anchors. 5. n-pentenyl ortho esters for mannan components
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Procedures for rapid assembly of multigram amounts of mannan components have been examined. Although these studies are reported in the context of the mannan moiety of the glycan anchors of membrane-bound glycoproteins, the procedures should be applicable
- Roberts, Carmichael,Madsen, Robert,Fraser-Reid, Bert
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p. 1546 - 1553
(2007/10/02)
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