MedKoo Cat#: 526790 | Name: X-NeuNAc

Description:

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

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

X-NeuNAc
X-NeuNAc
CAS#160369-85-7

Theoretical Analysis

MedKoo Cat#: 526790

Name: X-NeuNAc

CAS#: 160369-85-7

Chemical Formula: C19H21BrClN2NaO9

Exact Mass:

Molecular Weight: 559.73

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 currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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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

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
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.