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.


Price and Availability

Size
Price

Size
Price

Size
Price

CB-1339 (X-NeuNAc) is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 526790
Name: X-NeuNAc
CAS#: 160369-85-7
Chemical Formula: C19H21BrClN2NaO9
Exact Mass:
Molecular Weight: 559.7258
Elemental Analysis: C, 40.77; H, 3.78; Br, 14.28; Cl, 6.33; N, 5.00; Na, 4.11; O, 25.73


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+]


Technical Data

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).

Harmonized System Code:
293490


References

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.