X-NeuNAc

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526790

CAS#: 160369-85-7

Description: X-NeuNAc, also known as CB1339 and X-Neu5Ac, is a novel substrate for chromogenic assay of neuraminidase activity in bacterial expression systems. X-NeuNAc can be used to facilitate the screening of bacterial colonies or plaques for the detection of either natural or mutant neuraminidase activity. Preliminary kinetic studies indicate that this compound is a good substrate (Km 0.89 x 10(-3) M) for neuraminidase and is quite stable under identical conditions in the absence of enzyme. These results suggest that X-Neu5Ac can be useful to screen for bacterially-encoded enzyme production directly on agar plates.

Chemical Structure

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X-NeuNAc
CAS# 160369-85-7
Instruction

Theoretical Analysis

MedKoo Cat#: 526790
Name: X-NeuNAc
CAS#: 160369-85-7
Chemical Formula: C19H21BrClN2NaO9
Exact Mass: 0.00
Molecular Weight: 559.726
Elemental Analysis: C, 40.77; H, 3.78; Br, 14.28; Cl, 6.33; N, 5.00; Na, 4.11; O, 25.73

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: X-Neu5Ac; CB-1339; 160369-85-7; X-NeuNAc.

IUPAC/Chemical Name: sodium;(2S,4S,5R,6R)-5-acetamido-2-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

InChi Key: MNWWXEDVLXNFDD-GNZCRVNMSA-M

InChi Code: InChI=1S/C19H22BrClN2O9.Na/c1-7(25)23-15-10(26)4-19(18(29)30,32-17(15)16(28)11(27)6-24)31-12-5-22-9-3-2-8(20)14(21)13(9)12;/h2-3,5,10-11,15-17,22,24,26-28H,4,6H2,1H3,(H,23,25)(H,29,30);/q;+1/p-1/t10-,11+,15+,16+,17+,19+;/m0./s1

SMILES Code: O=C([C@]1(OC2=CNC3=C2C(Cl)=C(Br)C=C3)O[C@@H]([C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C1)[O-].[Na+]

Appearance: White to off-white solid powder.

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 559.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Minami A, Shimizu H, Meguro Y, Shibata N, Kanazawa H, Ikeda K, Suzuki T. Imaging of sialidase activity in rat brain sections by a highly sensitive fluorescent histochemical method. Neuroimage. 2011 Sep 1;58(1):34-40. doi: 10.1016/j.neuroimage.2011.06.017. Epub 2011 Jun 16. PubMed PMID: 21703353.

2: Kerr CL, Hanna WF, Shaper JH, Wright WW. Lewis X-containing glycans are specific and potent competitive inhibitors of the binding of ZP3 to complementary sites on capacitated, acrosome-intact mouse sperm. Biol Reprod. 2004 Sep;71(3):770-7. Epub 2004 May 5. PubMed PMID: 15128590.

3: Saito M, Hagita H, Ito M, Ando S, Yu RK. Age-dependent reduction in sialidase activity of nuclear membranes from mouse brain. Exp Gerontol. 2002 Jul;37(7):937-41. PubMed PMID: 12086703.

4: Saito M, Hagita H, Iwabuchi Y, Fujii I, Ikeda K, Ito M. Fluorescent cytochemical detection of sialidase activity using 5-bromo-4-chloroindol-3-yl-alpha- D- N-acetylneuraminic acid as the substrate. Histochem Cell Biol. 2002 May;117(5):453-8. Epub 2002 Apr 6. PubMed PMID: 12029493.

5: Horie K, Sakagami M, Kuramochi K, Hanasaki K, Hamana H, Ito T. Enhanced accumulation of sialyl Lewis X-carboxymethylpullulan conjugate in acute inflammatory lesion. Pharm Res. 1999 Feb;16(2):314-20. PubMed PMID: 10100320.

6: Kogan TP, Revelle BM, Tapp S, Scott D, Beck PJ. A single amino acid residue can determine the ligand specificity of E-selectin. J Biol Chem. 1995 Jun 9;270(23):14047-55. PubMed PMID: 7539797.

7: Fujii I, Iwabuchi Y, Teshima T, Shiba T, Kikuchi M. X-Neu5Ac: a novel substrate for chromogenic assay of neuraminidase activity in bacterial expression systems. Bioorg Med Chem. 1993 Aug;1(2):147-9. PubMed PMID: 8081844.

8: Suzuki Y, Toda Y, Tamatani T, Watanabe T, Suzuki T, Nakao T, Murase K, Kiso M, Hasegawa A, Tadano-Aritomi K, et al. Sulfated glycolipids are ligands for a lymphocyte homing receptor, L-selectin (LECAM-1), Binding epitope in sulfated sugar chain. Biochem Biophys Res Commun. 1993 Jan 29;190(2):426-34. PubMed PMID: 7678958.

9: Berg EL, Magnani J, Warnock RA, Robinson MK, Butcher EC. Comparison of L-selectin and E-selectin ligand specificities: the L-selectin can bind the E-selectin ligands sialyl Le(x) and sialyl Le(a). Biochem Biophys Res Commun. 1992 Apr 30;184(2):1048-55. PubMed PMID: 1374233.