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568600 Sigma-Aldrich

6-Maleimidohexanoic acid N-hydroxysuccinimide ester

98%

Synonym: 6-Maleimidocaproic acid N-succinimidyl ester, N-(ε-Maleimidocaproyloxy)succinimide, N-Succinimidyl 6-maleimidocaproate, EMCS

  • CAS Number 55750-63-5

  • Empirical Formula (Hill Notation) C14H16N2O6

  • Molecular Weight 308.29

  •  Beilstein/REAXYS Number 1499815

  •  MDL number MFCD00043043

  •  PubChem Substance ID 24880215

  •  NACRES NA.22

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Properties

Related Categories Amine to Sulfhydryl, Building Blocks, Carbonyl Compounds, Chemical Biology, Chemical Synthesis,
Quality Level   100
assay   98%
reaction suitability   reagent type: cross-linking reagent
mp   70-73 °C (lit.)
SMILES string   O=C(CCCCCN1C(=O)C=CC1=O)ON2C(=O)CCC2=O
InChI   1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2
InChI key   VLARLSIGSPVYHX-UHFFFAOYSA-N

Description

Application

6-Maleimidohexanoic acid N-hydroxysuccinimide ester can be used in:
• Synthesis of maleimide-activated carbohydrates for site-specific glycosylation of cysteine-containing peptides and proteins via maleimide-thiol ligation reaction.
• Synthesis of a glucuronide prodrug of doxorubicin bearing a maleimide side chain as an antitumor agent.
• Cross-linking oligonucleotides with the amino groups on the substrate to fabricate DNA microarrays.

Packaging

500 mg in amber glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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