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63174

Sigma-Aldrich

4-Maleimidobutyric acid

≥98.0% (T)

Synonym(s):

γ-Maleimidobutyric acid, 4-Maleimidobutanoic acid, N-(3-Carboxypropyl)maleimide, N-Maleoyl-4-aminobutyric acid, N-Maleoyl-GABA

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About This Item

Empirical Formula (Hill Notation):
C8H9NO4
CAS Number:
57078-98-5
Molecular Weight:
183.16
Beilstein:
1455876
MDL number:
MFCD00043139
UNSPSC Code:
12352106
PubChem Substance ID:
329759801
NACRES:
NA.25

Quality Level

100

Assay

≥98.0% (T)

mp

95-98 °C

SMILES string

OC(=O)CCCN1C(=O)C=CC1=O

InChI

1S/C8H9NO4/c10-6-3-4-7(11)9(6)5-1-2-8(12)13/h3-4H,1-2,5H2,(H,12,13)

InChI key

NCPQROHLJFARLL-UHFFFAOYSA-N

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Application

Gamma-maleimidobutyric acid may be used as a spacer in the construction of drug and other types of bioconjugates. 4-Maleimidobutyric acid is used with N-hydroxysuccinimide ester as a bifunctional cross-linking agent.
Modification reagent for thiol groups in proteins

Other Notes

SH-label for the modification of peptides and proteins; Used for the preparation of a new bleomycin analog for enzyme immunoassay (EIA); probe for membrane SH-groups

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBS9292V
BCBR2680V
1431812V
1431812
1348754

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Biochemical Society Transactions, 11, 753-753 (1983)
K Fujiwara et al.
Cancer research, 41(10), 4121-4126 (1981-10-01)
An antibody directed toward pepleomycin, a new antitumor antibiotic related structurally to bleomycin, has been produced in rabbits by immunization with a pepleomycin-protein conjugate which was prepared by a novel procedure of coupling pepleomycin to mercaptosuccinylated bovine serum albumin using
N-polymethylenecarboxymaleimides -- a new class of probes for membrane sulphydryl groups.
D G Griffiths et al.
FEBS letters, 134(2), 261-263 (1981-11-16)
Weibo Cai et al.
Nature protocols, 3(1), 89-96 (2008-01-15)
To take full advantage of the unique optical properties of quantum dots (QDs) and expedite future near-infrared fluorescence (NIRF) imaging applications, QDs need to be effectively, specifically and reliably directed to a specific organ or disease site after systemic administration.
Marie Pribylova et al.
International journal of pharmaceutics, 415(1-2), 175-180 (2011-06-15)
A new targeted conjugates in which paclitaxel was used as a cytostatic compound and an analog of the gonadotropin-releasing hormone (GnRH) as a targeting moiety were synthesized. The molecule of the peptide hormone GnRH was modified to allow its connection
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