394815

Sigma-Aldrich

N-Maleoyl-β-alanine

greener alternative

97%

Synonym(s):
3-Maleimidopropionic acid, N-(2-Carboxyethyl)maleimide
Empirical Formula (Hill Notation):
C7H7NO4
CAS Number:
Molecular Weight:
169.13
Beilstein/REAXYS Number:
1528952
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

97%

greener alternative product score

old score: 17
new score: 6
Find out more about DOZN™ Scoring.

greener alternative product characteristics

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

mp

103-106 °C (lit.)

greener alternative category

Re-engineered

storage temp.

2-8°C

SMILES string

OC(=O)CCN1C(=O)C=CC1=O

InChI

1S/C7H7NO4/c9-5-1-2-6(10)8(5)4-3-7(11)12/h1-2H,3-4H2,(H,11,12)

InChI key

IUTPJBLLJJNPAJ-UHFFFAOYSA-N

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General description

N-Maleoyl-β-alanine (3-maleimidopropanoic acid) is an aliphatic N-substituted maleimide. It is one of the component of the stabilizing solution for EC145 (a folate-targeted vinca alkaloid conjugate) used in rodent pharmacokinetic studies.

Application

N-Maleoyl-β-alanine (3-maleimidopropanoic acid, N-(2-carboxyethyl)maleimide)) is the suitable reagent used in the following studies:
  • To decrease the biotin binding affinity of Avd(S16C) (avidin with a single point mutation S16C).
  • As a side chain reactive agent to modify tryptic peptides that result in mass shifts indicating the presence of cysteine residues.
  • To preblock Xenopus laevis oocytes for exposed cysteines used as an expression system in the study of conformational changes in cASIC1a Receptors.
It may be used in the following studies:
  • As a protective agent for keratin fiber in high temperature process.
  • As a non-cleavable maleimido moiety during the synthesis of tetrawalled molecular umbrella-octaarginine conjugates.
  • Synthesis of organotin carboxylates of N-Maleoyl-β-alanine.
  • To functionalize the gold surfaces to interact with cysteine-modified peptide.
  • Preparation of cross-linked dextran–poly(ethylene glycol) hydrogel substrate.

Packaging

1 g in glass bottle
250 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Organotin (IV) derivatives of N-maleoylamino acids: their synthesis and structural elucidation.
Bhatti MH, et al
Turkish Journal of Chemistry, 29(5), 463-476 (2005)
Swarna S Ramaswamy et al.
The Journal of biological chemistry, 288(50), 35896-35903 (2013-11-08)
Acid-sensing ion channels are cation channels activated by external protons and play roles in nociception, synaptic transmission, and the physiopathology of ischemic stroke. Using luminescence resonance energy transfer (LRET), we show that upon proton binding, there is a conformational change...
Lauren L Cline et al.
Bioconjugate chemistry, 22(11), 2210-2216 (2011-10-12)
A series of diwalled and tetrawalled molecular umbrellas have been synthesized using cholic acid, spermidine, and lysine as starting materials. Coupling of these molecular umbrellas to an octaarginine peptide afforded agents that were capable of promoting the transport of small...
Néstor López Mora et al.
Chemical communications (Cambridge, England), 50(16), 1953-1955 (2014-01-11)
We present a novel chemically cross-linked dextran-poly(ethylene glycol) hydrogel substrate for the preparation of dense vesicle suspensions under physiological ionic strength conditions. These vesicles can be easily diluted for individual study. Modulating the degree of cross-linking within the hydrogel network...
Protecting keratin fiber with water soluble N-substituted maleimides in high temperature processes.
Cai JY, et al.
Fibers and Polymers, 15(11), 2247-2252 (2014)

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