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900917

Sigma-Aldrich

N-Azidoacetylmannosamine-tetraacylated

95%

Synonym(s):

Ac4ManNAz

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About This Item

Empirical Formula (Hill Notation):
C16H22N4O10
CAS Number:
361154-30-5
Molecular Weight:
430.37
MDL number:
MFCD26961126
UNSPSC Code:
12352116
NACRES:
NA.22
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Quality Level

100

Assay

95%

form

powder or crystals

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

SMILES string

[N+](=[N-])=NCC(=O)N[C@H]1[C@H]([C@@H]([C@H](OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C

InChI

1S/C16H22N4O10/c1-7(21)26-6-11-14(27-8(2)22)15(28-9(3)23)13(16(30-11)29-10(4)24)19-12(25)5-18-20-17/h11,13-16H,5-6H2,1-4H3,(H,19,25)/t11-,13+,14-,15-,16?/m1/s1

InChI key

HGMISDAXLUIXKM-LIADDWGISA-N

Related Categories

Application

N-Azidoacetylmannosamine-tetraacylated (Ac4ManNAz) is an azide-containing metabolic glycoprotein labeling reagent that can be incorporated into the sialic acid biosynthesis pathway. The azide-modified protein can be detected by reaction with alkynes. For example alkynes labeled with a fluorescent probe or a biotin can be used. The acetyl groups increase cell permeability and allow the unnatural sugars to easily pass through the cell membrane. Carboxyesterases remove the acetyl groups once the monosaccharide is in the cell.
Tetraacylated N-azidoacetylmannosamine is generally used in click chemistry applications in bioconjugate chemistry.[1][2][3][4]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT7099
MKCT1471
MKCR3430
MKCP8433
MKCN7956

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Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones.
Jewett J C, et al.
Journal of the American Chemical Society, 132(11), 3688-3690 (2010)
Carbohydrate?neuroactive hybrid strategy for metabolic glycan engineering of the central nervous system in vivo.
Shajahan A, et al.
Journal of the American Chemical Society, 139(2), 693-700 (2017)
Coupling of Immunostimulants to Live Cells through Metabolic Glycoengineering and Bioorthogonal Click Chemistry.
Mongis A, et al.
Bioconjugate Chemistry, 28(4), 1151-1165 (2017)
Bioorthogonal Click Chemistry?Based Synthetic Cell Glue.
Koo H , et al.
Small, 11(48), 6458-6466 (2015)

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Crosslinkers Selection Guide

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Crosslinkers Selection Guide

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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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