355012-91-8

Usage

Chemical Properties

White Solid

Uses

D-(+)-Cellohexose Eicosaacetate (cas# 355012-91-8) is a compound useful in organic synthesis.

Upstream product

• 108-24-7 acetic anhydride 
• 23661-37-2 α-cyclodextrin peracetate 
• 10016-20-3 alpha cyclodextrin 
• 1184-46-9 cellohexaose 
• 1184-46-9 Maltohexaose 
• 1600-27-7 mercury(II) diacetate 
• 1184-46-9 D-maltohexaose 

Relevant academic research and scientific papers

Synthesis, conformation and T-helper cell stimulation of an O-linked glycopeptide epitope containing extended carbohydrate side-chains

To answer the question whether or not T cells to immunodominant protein fragments recognize glycosylated antigens, we synthesized a series of glycopeptides corresponding to peptide 31D, a major T-helper cell epitope of the rabies virus nucleoprotein. Thr4 of the epitope is known to allow mono- or disaccharide side-chain substitutions in either α- or β-anomeric configuration without interfering with MHC-binding. To model naturally occurring glycoprotein fragments that carry extended sugar chains, we prepared Fmoc-Ser/Thr-OPfp building blocks containing α- and β-linked linear tri- and heptasaccharides. Peptide 31D was synthesized with the complex carbohydrates attached to Thr4, and the T-helper cell activity of the glycopeptides was determined. Addition of α-linked carbohydrates, that mimic most of the natural O-linked glycoproteins, resulted in a major drop in the T-cell stimulatory ability in a sugar length-dependent manner. In contrast, the cytosolic glycoprotein mimicking β-linked glycopeptides retained their T-cell stimulatory activity, with the trisaccharide-containing analogue being almost as potent as the unglycosylated peptide. When the peptides were preincubated with diluted human serum, all peptides lost their ability to stimulate the 9C5.D8-H hybridoma. These findings indicated that (i) in contrast to cytosolic glycosylation, incorporation of long O-linked carbohydrates into T-helper cell epitopes abrogates the antigenicity of these protein fragments, and (ii) glycosylation is not a viable alternative to improve the immunogenic properties of subunit peptide vaccines. Glycosylation with all four carbohydrate moieties similarly destroyed the inducible α-helical structure of peptide 31D as detected by CD, indicating that the differences in the T-cell activity were not due to different peptide conformations.

Synthesis of regioselectively and uniformly modified maltoheptaose derivatives from cyclomaltoheptaose precursors

Heptadeoxy-6I-VII-halo, -azido, and hepta-6I-VII S-hepta(N-Boc-2-amino)ethyl-6I-VII-heptathiomaltoheptaose derivatives were prepared by acetolysis of the corresponding per-C-6-modified β-cyclodextrin derivatives. The rapid

Maltotriose-based probes for fluorescence and photoacoustic imaging of bacterial infections

Currently, there are no non-invasive tools to accurately diagnose wound and surgical site infections before they become systemic or cause significant anatomical damage. Fluorescence and photoacoustic imaging are cost-effective imaging modalities that can be used to noninvasively diagnose bacterial infections when paired with a molecularly targeted infection imaging agent. Here, we develop a fluorescent derivative of maltotriose (Cy7-1-maltotriose), which is shown to be taken up in a variety of gram-positive and gram-negative bacterial strains in vitro. In vivo fluorescence and photoacoustic imaging studies highlight the ability of this probe to detect infection, assess infection burden, and visualize the effectiveness of antibiotic treatment in E. coli-induced myositis and a clinically relevant S. aureus wound infection murine model. In addition, we show that maltotriose is an ideal scaffold for infection imaging agents encompassing better pharmacokinetic properties and in vivo stability than other maltodextrins (e.g. maltohexose).

MALTOTRIOSE-BASED PROBES FOR FLUORESCENCE AND PHOTOACOUSTIC IMAGING OF BACTERIA

Embodiments of the present disclosure provide for labeled maltotriose probes, methods of making labeled probes, pharmaceutical compositions including labeled probes, methods of using labeled probes, methods of diagnosing, localizing, monitoring, and/or assessing bacterial infections, using labeled probes, kits for diagnosing, localizing, monitoring, and/or assessing bacterial infections, using labeled probes, and the like.

Oligosaccharide conjugates for targeting bacteria and uses related thereto

This disclosure relates to conjugates for targeting bacteria and related uses. In certain embodiments, the disclosure relates to methods of transferring a molecule of interest into bacteria comprising mixing bacteria with a non-naturally occurring conjuga

Glycodynamers: Dynamic polymers bearing oligosaccharides residues - Generation, structure, physicochemical, component exchange, and lectin binding properties

Dynamic glycopolymers have been generated by polycondensation through acylhydrazone formation between components bearing lateral bioactive oligosaccharide chains. They have been characterized as bottlebrush type by cryo-TEM and SANS studies. They present remarkable fluorescence properties whose emission wavelengths depend on the constitution of the polymer and are tunable by constitutional modification through exchange/Incorporation of components, thus also demonstrating their dynamic character. Constitution-dependent binding of these glycodynamers to a lectin, peanut agglutinin, has been demonstrated.

Oligosaccharide analogues of polysaccharides part 22: Synthesis of cyclodextrin analogues containing a buta-1,3-diyne-1,4-diyl or a butane-1,4-diyl unit

The peracetylated hexaamylose (maltohexaose) 18 was obtained by an improved acetolysis of cyclomaltohexaose (α-cyclodextrin, α-CD, 16), and transformed into the benzyl- and 4-chlorobenzyl-protected thioglycosides 22 and 23, respectively (Scheme 2). Sequen

Studies of the series of cellooligosaccharide peracetates as a model for cellulose triacetate by 13C CP/MAS NMR spectroscopy and X-ray analyses

The series of crystalline oligomers from α-cellobiose octaacetate through α-cellohexaose eicosaacetate, listed as below, was prepared from homogeneous acetylation of the corresponding cellooligosaccharides and characterized by 13C CP/MAS NMR spectroscopy and X-ray analysis in order to obtain the structural models of cellulose triacetate (CTA) in solid state. Progressing toward the hexamer, the NMR spectral feature of the oligomers, in comparison with two allomorphs of CTA I and CTA II, gradually approached that of CTA I. Specifically, chemical shifts of both the hexamer and the pentamer were in considerable respective agreement with those of CTA I. In addition, X-ray diffraction patterns of the oligomers established that the crystalline pentamer and hexamer have a CTA I lattice in spite of recrystallization from ethylacetate-hexane. We therefore concluded that the pentamer and hexamer would be useful models for the CTA I structure. Copyright (C) 1999 Elsevier Science Ltd.

Isolation, modification, and NMR assignments of a series of cellulose oligomers

A homologous series of cellulose oligomers from two to eight repeating subunits have been isolated and size-fractionated from the hydrolysis products of microcrystalline cellulose. Chemical modification of cellotriose (1), cellotetraose (2), cellopentaose (3), and cellohexaose (4) to the corresponding β-methyl glycosides 13-16 proceeded in three steps in overall yields of 16-46%. Peracetylation produced oligomers 5-8 in 70-75% yield, and subsequent formation of the β-methyl glycosides gave 9-12 in 42-89% yield. Removal of the acetate-protecting groups employing guanidine provided 13-16 in 73-79% yield. This modification eliminated anomeric equilibration and permitted a detailed NMR solution study of these oligomers. The complete 1H and 13C chemical shift assignments of each peracetylated and deprotected oligomer were obtained through a combination of DQF-COSY, HMQC, HMBC, and HMQC-TOCSY experiments. All the resonances in methyl cellotriose (13) and methyl cellotetraose (14) were readily distinguishable from one another and directly assignable. Severe overlap of the resonances for the inner pyranose rings of methyl cellopentaose (15) and methyl cellohexaose (16) was observed and could only be resolved and assigned using a comprehensive battery of 3D pulse sequences. These results demonstrate the utility of multidimensional NMR experiments in assigning the signals from a repeating polysaccharide and represent the first necessary step in a comprehensive, systematic study of cellulose oligomers in solution.