123483-77-2Relevant articles and documents
A silyl ether-protected building block forO-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection
Yan, Bingjia,Li, Wenyi,Hackenberger, Christian P. R.
supporting information, p. 8014 - 8017 (2021/10/04)
In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linkedO-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.
Synthesis method of tetrahydropyrano [3, 2-d] oxazole ring compound
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Paragraph 0017-0018, (2021/01/15)
The invention discloses a tetrahydropyrano [3, 2d] oxazole ring compound and a synthesis method thereof.The synthesis method includes the following steps that a sealed container A and a sealed container B are designed, the tops of the two sealed containers are communicated through a guide pipe, 2-acetamido-2-deoxy-D-pyranose protected by a protecting group is added into the container A, - and 1, 1-sulfonyldiimidazole andpotassium fluoride are added into the container B, dichloromethane and triethylamine are injected into the container A, and trifluoroacetic acid is injected into the containerB, sulfuryl fluoride gas is generated in situ in the container B, the sulfuryl fluoride gas is introduced into the container A through a conduit, stirring and reacting are carried out in the containerA, reduced pressure spin-drying is carried out after the reaction is completed, and silica gel rapid column chromatography separation is carried out to obtain the target compound. The process for preparing the tetrahydropyrano [3, 2-d] oxazole ring compound is simple, the yield of the target compound is high, and the substrate range is wide. And the reaction can be carried out at normal temperature, and the method is simple, convenient to operate and suitable for conventional preparation.
Dual-participation protecting group solves the anomeric stereocontrol problems in glycosylation reactions
Liu, Hui,Hansen, Thomas,Zhou, Si-Yu,Wen, Guo-En,Liu, Xu-Xue,Zhang, Qing-Ju,Codeé, Jeroen D. C.,Schmidt, Richard R.,Sun, Jian-Song
, p. 8713 - 8717 (2019/10/28)
The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.
Water-soluble Glucosamine-coated AIE-Active Fluorescent Organic Nanoparticles: Design, Synthesis and Assembly for Specific Detection of Heparin Based on Carbohydrate–Carbohydrate Interactions
Ji, Yan-ming,Liu, Guang-jian,Li, Cui-yun,Liu, Yi-chen,Hou, Min,Xing, Guo-wen
supporting information, p. 3295 - 3300 (2019/11/05)
Two water-soluble carbohydrate-coated AIE-activate fluorescent organic nanoparticles TPE3G and TPE4G were designed and synthesized for the detection of heparin. Different from the reported strategy, we not only utilized the general detection mechanism of
Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives
Zheng, Changping,Bavaro, Teodora,Tengattini, Sara,Mascherpa, Andrea Gualla,Sollogoub, Matthieu,Zhang, Yongmin,Terreni, Marco
supporting information, p. 3622 - 3631 (2019/06/17)
Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.
Design, Synthesis, and Preliminary Biological Evaluation of GlcNAc-6P Analogues for the Modulation of Phosphoacetylglucosamine Mutase 1 (AGM1/PGM3)
Paiotta, Alice,D'Orazio, Giuseppe,Palorini, Roberta,Ricciardiello, Francesca,Zoia, Luca,Votta, Giuseppina,De Gioia, Luca,Chiaradonna, Ferdinando,La Ferla, Barbara
, p. 1946 - 1952 (2018/05/15)
A library of GlcNAc 6- or 1-phosphate analogues was designed, and each compound was evaluated computationally through docking studies for its binding affinity to AGM1/PGM3. The compounds with the highest binding affinity, as ranked through a docking score, were synthesised and screened for their ability to inhibit the production of UDP-GlcNAc. A glycofused oxazoline analogue showed good inhibition, and gave significant results in vitro.
COMPOSITIONS AND METHODS FOR INDUCING IMMUNE TOLERANCE
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Paragraph 0311; 0312, (2019/01/08)
Several embodiments provided in the present disclosure relate to compositions that carry an antigen to which tolerance is desired, the antigen being coupled, bound, or otherwise joined to a targeting moiety, the targeting moiety configured to direct the composition to the liver of a subject. In several embodiments, the antigen in coupled to the targeting moiety by way of a polymeric linker. In several embodiments, the polymeric linker is configured to liberate the antigen in vivo. Methods of using the compositions to reduce and/or prevent unwanted immune responses against an antigen of interest are also provided.
Glycosyl Aldehydes: New Scaffolds for the Synthesis of Neoglycoconjugates via Bioorthogonal Oxime Bond Formation
Reina, José J.,Rioboo, Alicia,Montenegro, Javier
, p. 831 - 845 (2018/01/11)
The straightforward preparation of glycosyl neoconjugates by oxime (or hydrazone) bond formation represents a key bioorthogonal tool in chemical biology. However, when this strategy is employed by reacting the reducing end of the glycan moiety, the configuration and the stereochemical information is lost due to partial (or complete) opening of the glycan cyclic hemiacetal and the formation of the corresponding opened tautomers. We have completed the synthesis of a library of glycosyl aldehydes to be used as scaffold for the synthesis of neoglycoconjugates via oxime bond formation. These glycosyl aldehydes constitute a simple and accessible alternative to avoid loss of chiral information when conjugating, by oxime (or hydrazone) bonds, the aldehyde functionality present at the reducing end of natural carbohydrates.
Simple and Efficient Preparation of O- and S-GlcNAcylated Amino Acids through InBr3-Catalyzed Synthesis of β- N-Acetylglycosides from Commercially Available Reagents
De Leon, Cesar A.,Lang, Geoffrey,Saavedra, Marcos I.,Pratt, Matthew R.
supporting information, p. 5032 - 5035 (2018/08/24)
The facile synthesis of serine, threonine, and cysteine β-glycosides using commercially available peracetylated β-N-acetylglucosamine (β-Ac4GlcNAc) and catalytic amounts of indium bromide (InBr3) is described. This method involves only inexpensive reagents that require no further modification or special handling. The reagents are simply mixed, dissolved, and refluxed to afford the GlcNAcylated amino acids in great yields (70-80%). This operationally simple procedure should facilitate the study of O-GlcNAcylation without necessitating expertise in synthetic carbohydrate chemistry.
ENDOSOMAL CLEAVABLE LINKERS
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Paragraph 00565, (2018/08/20)
The present disclosure relates generally to cleavable linkers and uses thereof.