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129585

Sigma-Aldrich

Maleimide

99%

Synonym(s):

2,5-Pyrroledione

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About This Item

Empirical Formula (Hill Notation):
C4H3NO2
CAS Number:
541-59-3
Molecular Weight:
97.07
Beilstein/REAXYS Number:
106910
EC Number:
208-787-4
MDL number:
MFCD00005494
UNSPSC Code:
12352100
PubChem Substance ID:
24847914
NACRES:
NA.22

Quality Level

200

assay

99%

form

powder

mp

91-93 °C (lit.)

SMILES string

O=C1NC(=O)C=C1

InChI

1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)

InChI key

PEEHTFAAVSWFBL-UHFFFAOYSA-N

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General description

Maleimide (2,5-Pyrroledione) is a new nanoparticle surface functional group which favors easy conjugation with cell penetration peptides. The conjugation is enabled via click chemistry to preserve its biofunctions.

Maleimide is used as a dienophile in Diels Alder reaction for the synthesis of macromolecules.

Application

Rhodium-catalyzed conjugate arylation with arylboronic acids.
The maleimide-functionalized silica beads were used to immobilize the bovine serum albumin (BSA)-boronic acid (BA) conjugates.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The furan/maleimide Diels--Alder reaction: A versatile click--unclick tool in macromolecular synthesis
Gandini A.
Progress in Polymer Science, 38, 1-29 (2013)
Tetrahedron Letters, 48, 4413-4413 (2007)
Paulo L Onuchic et al.
Scientific reports, 9(1), 12161-12161 (2019-08-23)
Liquid-liquid phase separation (LLPS) of RNA-protein complexes plays a major role in the cellular function of membraneless organelles (MLOs). MLOs are sensitive to changes in cellular conditions, such as fluctuations in cytoplasmic ion concentrations. To investigate the effect of these
Meng Ke et al.
PLoS computational biology, 13(6), e1005603-e1005603 (2017-06-16)
GLUT1 facilitates the down-gradient translocation of D-glucose across cell membrane in mammals. XylE, an Escherichia coli homolog of GLUT1, utilizes proton gradient as an energy source to drive uphill D-xylose transport. Previous studies of XylE and GLUT1 suggest that the
Guangxue Feng et al.
Small (Weinheim an der Bergstrasse, Germany), 10(6), 1212-1219 (2013-12-18)
Single-chain conjugated polymer (CP) dots embedded nanoparticles (NPs) bearing cell penetration peptide (TAT) as surface ligands are synthesized for long term cancer cell tracing applications. The CPNPs are fabricated by matrix-encapsulation method and the embedded CPs can be modulated into
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