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Chemical Structure| 5505-63-5 Chemical Structure| 5505-63-5
Chemical Structure| 5505-63-5

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CAS No.: 5505-63-5

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(2S,3R,4S,5R)-2-Amino-3,4,5,6-tetrahydroxyhexanal hydrochloride is an endogenous metabolite.

Synonyms: D-Mannosamine hydrochloride; Mannosamine HCl; Mannosamine hydrochloride

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Zhao, Yue ; Lyu, Zhigang ; Prather, Benjamin ; Lewis, Todd R ; Kang, Jinfeng ; Wang, Rongsheng E

Abstract: Dysregulated sialic acid biosynthesis is characteristic of the onset and progression of human diseases including hormone-sensitive prostate cancer and breast cancer. The sialylated glycoconjugates involved in this process are therefore important targets for identification and functional studies. To date, one of the most common strategies is metabolic glycoengineering, which utilizes N-acetylmannosamine (ManNAc) analogues such as N-azidoacetylmannosamine (ManNAz) to hijack sialic acid biosynthesis and label the sialylated glycoconjugates with "click chemistry (CuAAC)" tags. Yet, current chemical modifications including those CuAAC-based alkyne/azide tags are still big in size, and the resulting steric hindrance perturbs the mannosamine and sialic acid derivatives' recognition and metabolism by enzymes involved in biosynthetic pathways. As a result, the peracetylated ManNAz has compromised incorporation to sialic acid substrates and manifests cellular growth inhibition and cytotoxicity. Herein, we show that the α-fluorinated peracetylated analogue ManN(F-Ac) displayed a satisfying safety profile in mammalian cell lines at concentrations as high as 500 μM. More importantly, aliphatic selenol-containing probes can efficiently displace α-fluorine in fluoroacetamide-containing substrates including ManN(F-Ac) at a neutral pH range (~7.2). The combined use of peracetylated ManN(F-Ac) and the dethiobiotin-selenol probe as the fluorine-selenol displacement reaction (FSeDR) toolkit allowed for successful metabolic labeling of sialoglycoproteins in multiple prostate and cancer cell lines, including PC-3 and MDA-MB-231. More sialoglycoproteins in these cell lines were demonstrated to be labeled by FSeDR compared with the traditional CuAAC approach. Lastly, with FSeDR-mediated metabolic labeling, we were able to probe the cellular expression level and spatial distribution of sialylated glycoconjugates during the progression of these hormone-sensitive cancer cells. Taken together, the promising results suggest the potential of the FSeDR strategy to efficiently and systematically identify and study sialic acid substrates and potentially empower metabolic engineering on a diverse set of glycosylated proteins that are vital for human diseases.

Keywords: metabolic engineering ; mannosamine ; sialic acid ; glycobiology ; fluorine displacement reaction ; selenium ; fluorine-selenol displacement reaction (FSeDR)

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Chen, Jing ; Ji, Peng ; Gnawali, Giri ; Chang, Mengyang ; Gao, Feng ; Xu, Hang , et al.

Abstract: The current targeting drug delivery mainly relies on cancer cell surface receptors. However, in many cases, binding affinities between protein receptors and homing ligands is relatively low and the expression level between cancer and normal cells is not significant. Distinct from conventional targeting strategies, we have developed a general cancer targeting platform by building artificial receptor on cancer cell surface via a chemical remodeling of cell surface glycans. A new tetrazine (Tz) functionalized chemical receptor has been designed and efficiently installed on cancer cell surface as "overexpressed" biomarker through a metabolic glycan engineering. Different from the reported bioconjugation for drug targeting, the tetrazine labeled cancer cells not only locally activate TCO-caged prodrugs but also release active drugs via the unique bioorthogonal Tz-TCO click-release reaction. The studies have demonstrated that the new drug targeting strategy enables local activation of prodrug, which ultimately leads to effective and safe cancer therapy.

Keywords: Artificial receptor ; Click and release ; Local activation ; Protein degradation

Alternative Products

Product Details of D-Mannosamine HCl

CAS No. :5505-63-5
Formula : C6H14ClNO5
M.W : 215.63
SMILES Code : O=C[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO.[H]Cl
Synonyms :
D-Mannosamine hydrochloride; Mannosamine HCl; Mannosamine hydrochloride
MDL No. :MFCD09880213
InChI Key :CBOJBBMQJBVCMW-MVNLRXSJSA-N
Pubchem ID :9899264

Safety of D-Mannosamine HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
 

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Technical Information

? Appel Reaction ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Bucherer-Bergs Reaction ? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Chugaev Reaction ? Clemmensen Reduction ? Complex Metal Hydride Reductions ? Corey-Chaykovsky Reaction ? Corey-Fuchs Reaction ? Corey-Kim Oxidation ? Dess-Martin Oxidation ? Fischer Indole Synthesis ? Grignard Reaction ? Hantzsch Dihydropyridine Synthesis ? Heat of Combustion ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Jones Oxidation ? Julia-Kocienski Olefination ? Knoevenagel Condensation ? Leuckart-Wallach Reaction ? Mannich Reaction ? Martin's Sulfurane Dehydrating Reagent ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Mitsunobu Reaction ? Moffatt Oxidation ? Mukaiyama Aldol Reaction ? Nozaki-Hiyama-Kishi Reaction ? Oxidation of Alcohols by DMSO ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Alcohols ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Prins Reaction ? Reactions of Alcohols ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions with Organometallic Reagents ? Reformatsky Reaction ? Ritter Reaction ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Sharpless Olefin Synthesis ? Specialized Acylation Reagents-Vilsmeier Reagent ? Stetter Reaction ? Stobbe Condensation ? Swern Oxidation ? Tebbe Olefination ? Ugi Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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