289712-58-9

Upstream product

• 289712-57-8 2-(azidomethyl)benzoic acid 
• 329781-57-9 methyl 2-(azidomethyl) benzoate 
• 2417-73-4 methyl 2-bromomethylbenzoate 
• 89-71-4 2-Methyl-benzoic acid methyl ester 
• 118-90-1 ortho-methylbenzoic acid 
• 933-88-0 ortho-toluoyl chloride 

Downstream Products

• 289712-61-4 2-azidomethyl-N-[9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 
• 329781-62-6 2-azidomethyl-N-[9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-benzamide 
• 289712-62-5 2-Azidomethyl-N-[1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 
• 289712-59-0 2-Azidomethyl-benzoic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 385422-02-6 dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl phosphate 
• 385422-08-2 dibutyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-galactopyranosyl phosphate 
• 385421-98-7 n-pentenyl 4-O-(2-(azidomethyl)benzoyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 385422-04-8 thioethyl 2-O-(2-(azidomethyl)benzoyl)-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 385421-92-1 methyl 2-O-acetyl-6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-β-D-glucopyranoside 
• 385421-94-3 methyl 2-O-allyl-6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-β-D-glucopyranoside 
• 385421-97-6 methyl 2-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-6-O-tri-isopropylsilyl-β-D-glucopyranoside 
• 385421-93-2 methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-levulinyl-β-D-glucopyranoside 
• 385421-95-4 methyl 6-O-(2-(azidomethyl)benzoyl)-3,4-di-O-benzyl-2-O-p-methoxybenzyl-β-D-glucopyranoside 
• 385421-99-8 n-pentenyl 4-(2-(azidomethyl)benzoyl)-3,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Iridium(iii) complex-based electrochemiluminescent probe for H2S

Since abnormal levels of hydrogen sulphide (H2S) correlate with various diseases, simple methods for its rapid and sensitive detection are highly required. Herein, we introduce a new electrochemiluminescent probe 1 for H2S based on a cyclometalated iridium(iii) complex. o-(Azidomethyl)benzoate ester groups on the main ligands of probe 1 react selectively with H2S, resulting in cascade reactions involving H2S-mediated reduction and intramolecular cyclization/ester cleavage. With this structural change induced by H2S, the intrinsic electrochemiluminescence (ECL) of 1 decreased greatly due to the unfavourable electron transfer of a tripropylamine (TPA) radical. Probe 1 showed a high ECL turn-off ratio and good selectivity for H2S over various anions and biothiols. The sensing mechanism of H2S was elucidated using1H NMR spectroscopy and MALDI-TOF mass spectrometry analyses.

Performance comparison of two cascade reaction models in fluorescence off-on detection of hydrogen sulfide

Comparative studies on the performances of two cascade reaction based fluorescent H2S probes are reported. These probes were also designed to address the solubility issues of existing probes. The Reso-N3 probe favors the H2S mediated azide-to-amine reduction followed by a cyclization to release the resorufin fluorophore. Reso-Br undergoes a bromide-to-thiol nucleophilic substitution followed by a similar cyclization releasing the same fluorophore. Reso-N3 exhibited lower background fluorescence and better H2S sensing behavior in water compared to Reso-Br. Reso-Br underwent hydrolysis in aqueous buffer conditions (pH = 7.4) while, Reso-N3 was quite stable. Reso-N3 displayed high selectivity and sensitivity towards H2S. Live cell imaging of the species by the probe was also established. This journal is

Non-stoichiometric O-acetylation of Shigella flexneri 2a O-specific polysaccharide: Synthesis and antigenicity

Synthetic functional mimics of the O-antigen from Shigella flexneri 2a are seen as promising vaccine components against endemic shigellosis. Herein, the influence of the polysaccharide non-stoichiometric di-O-acetylation on antigenicity is addressed for the first time. Three decasaccharides, representing relevant internal mono- and di-O-acetylation profiles of the O-antigen, were synthesized from a pivotal protected decasaccharide designed to tailor late stage site-selective O-acetylation. The latter was obtained via a convergent route involving the imidate glycosylation chemistry. Binding studies to five protective mIgGs showed that none of the acetates adds significantly to broad antibody recognition. Yet, one of the five antibodies had a unique pattern of binding. With IC50 in the micromolar to submicromolar range mIgG F22-4 exemplifies a remarkable tight binding antibody against diversely O-acetylated and non-O-acetylated fragments of a neutral polysaccharide of medical importance. This journal is the Partner Organisations 2014.

Expanding the structural repertoire of β/α Ant-Pro (anthranilic acid-proline) oligomers into γ/α 2-Amb-Pro (2-aminomethyl benzoic acid-proline) oligomers

In this article, we report a novel class of heterogeneous synthetic oligomers featuring the conformationally constrained amino acid residues - 2-aminomethyl benzoic acid (2-Amb) and proline (Pro) in repeating sequences. Oligomers as large as hexadecamers featuring the conformationally restricted γ/α 2-Amb-Pro motif have been assembled using solution-phase Boc strategy, following multi-step synthetic sequences starting from the commercially available O-toluic acid. EDC-mediated peptide coupling has been found to be optimum for the assembly of the relatively non-polar oligomers, which could be readily purified by the standard column chromatographic purification procedures. This study offers considerable prospects of expanding the structural repertoire of β/α Ant-Pro motif, which has been described earlier to assume right-handed helical architecture displaying robust nine-membered-ring closed network of hydrogen-bonding interactions, into γ/α 2-Amb-Pro motif.

Chemical synthesis of bioactive siRNA in solution phase by using 2-(azidomethyl)benzoyl as 3′-hydroxyl group protecting group

A protecting group AZMB was introduced to ribonucleosides 3′-hydroxyl group to facilitate solution phase synthesis of siRNA. The protection and cleavage reaction were carried out in mild conditions, that is protection by acyl chloride and cleavage by triphenylphosphine. The synthesized siRNA showed good biological activity to suppress targeted superoxide dismutase gene expression.

METHOD FOR PREPARING OLIGONUCLEOTIDE

A method for preparing oligonucleotide comprising reacting the compound of Formula (1) with the compound of Formula (2) in a liquid reaction medium under the condition of condensation reaction to obtain the compound of formula (3). In the method according to the present invention, the functional groups are protected by suitable protective groups to only expose the 5′-OH of the compound of Formula (1) (OH-component) and the 3′-phosphate of the compound of Formula (2) (P-component) which are to be connected, so that the condensation reaction is carried out in a liquid reaction medium to bond the OH-component and P-component to obtain DNA or RNA short chain. The method of the present invention does not need a solid phase column and can be carried out in a liquid reaction medium. Thus, oligonucleotides can be synthesized on a large scale.

Novel O-acetylated decasaccharides

The present invention relates to diversely acetylated decasaccharides of formula (I) representative of two repeating units of Shigella flexneri serotype 2a O-antigen, conjugates and method of preparation thereof. These compounds exhibit antigenic properties and are particularly useful for the diagnosis of Shigella infection. wherein R1 and R2 are as defined in claim 1.

Synthesis of a tetrasaccharide substrate of heparanase

A tetrasaccharide, corresponding to the heparan sulfate heparanase substrate, namely β-d-GlcA(2S)-(1→4)-α-d-GlcN(NS,6S)-(1→4)-β-d-GlcA-(1→4)-α-d-GlcN(NS,6S)-OMe, was synthesized in a convergent manner via coupling of a pair of the disaccharide building blocks as a key step.

Novel preparation of (2-azidomethyl)benzoic acid and an application as a protective group

A novel preparation method of 2-(azidomethyl)benzoic acid, a precursor of (2-azidomethyl)benzoyl (AZMB) protective group, was developed which can provide pure sample in gram scale without chromatographic purifications. Reductive cleavage using triphenylphosphine was found to be effective in the case of sterically hindered ester that resists under basic hydrolysis.

Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks

A linear synthesis of a fully protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosyl trichloroacetimidate building blocks is reported. Envisioning an automated solid-phase synthesis of blood group determinants, the utility of glycosyl phosphates in the stepwise construction of complex oligosaccharides, such as the H-type II antigen, is demonstrated. Installation of the central glucosamine building block required the screening of a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally employed protecting groups was examined, as well as its use as a C2 stereodirecting group in glycosylations. The application of the 2-(azidomethyl)benzoyl group along with a systematic evaluation of glycosyl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that is expected to be generally amenable to the solid support synthesis of blood group determinants.