Endogenous metabolite.

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-Acetyl-D-mannosamine (Cyclic ManNAc) /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[1].

Lactiplantibacillus plantarum has been well acknowledged to produce exopolysaccharides (EPS) as a defense mechanism against acid stress. However, the complete biosynthetic pathway of EPS in L. plantarum and its impact on the cell growth and primary metabolism were still unclear. To fill these gaps, we carried out phenotypic, proteomic and metabolomics analysis of L. plantarum HMX2 cultured under different acidic conditions. Component and structure analysis showed that the repeating unit of EPS consisted of N-Acetyl-D-mannosamine (Cyclic ManNAc) /N-acetylmannosamine, N-acetylglucosamine, galactose, mannoses and glucoses. Multiomics analysis facilitated the curation and entablement of the complete EPS biosynthetic pathway ready for use in genome-scale metabolic models. Furthermore, proteomics and metabolomics data indicated that compared to the pH 6.5 condition, the acid stress at pH 4.5 significantly accelerated glycolysis and EPS biosynthesis processes while reduced the metabolic fluxes through the TCA cycle and the lactic acid fermentation, which suggested a trade-off between primary and secondary metabolism [2].

[1]. Metabolic Probing of Sialylated Glycoconjugates with Fluorine-Selenol Displacement Reaction (FSeDR). ACS Bio Med Chem Au. 2024 Dec 9;5(1):119-130.
[2]. Proteomics and metabolomics elucidate the biosynthetic pathway of acid stress-induced exopolysaccharides and its impact on growth phenotypes in Lactiplantibacillus plantarum HMX2. Food Chem. 2025 Feb 17:476:143431.

N-acetyl-beta-D-mannosamine is an N-acetyl-D-mannosamine having beta-configuration at its anomeric centre.
N-acetylmannosamine is under investigation for the other of GNE Myopathy.
N-Acetylmannosamine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
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C8H15NO6

221.2078

221.089

7772-94-3

N-Acetyl-D-mannosamine;3615-17-6

11096158

White to off-white solid powder

1.4±0.1 g/cm3

636.4±55.0 °C at 760 mmHg

130ºC

338.7±31.5 °C

0.0±4.3 mmHg at 25°C

1.542

-2.68

5

6

2

15

235

5

CC(=O)N[C@H]1[C@H]([C@@H]([C@H](O[C@H]1O)CO)O)O

OVRNDRQMDRJTHS-OZRXBMAMSA-N

InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5+,6-,7-,8-/m1/s1

2-(acetylamino)-2-deoxy-β-D-mannopyranose

7772-94-3; N-acetylmannosamine; N-((2R,3S,4R,5S,6R)-2,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide; N-Acetyl-beta-D-mannosamine; beta-ManNAc; N-[(2R,3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide; N-acetyl-beta-mannosamine; .beta.-D-Mannopyranose, 2-(acetylamino)-2-deoxy-;

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~452.06 mM)
H2O : ~100 mg/mL (~452.06 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (11.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (11.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (11.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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Solubility in Formulation 4: 100 mg/mL (452.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

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 (Please use freshly prepared in vivo formulations for optimal results.)