Name: N-Bromoacetyl-β-alanine
Brand: BOC Sciences
Rating: 5 (1 reviews)

Synonyms

3-(2-Bromoacetamido)propanoic acid; N-(Bromoacetyl)-beta-alanine

IUPAC Name

3-[(2-bromoacetyl)amino]propanoic acid

Canonical SMILES

C(CNC(=O)CBr)C(=O)O

InChI

InChI=1S/C5H8BrNO3/c6-3-4(8)7-2-1-5(9)10/h1-3H2,(H,7,8)(H,9,10)

InChIKey

ULKDIPSSLZFIQU-UHFFFAOYSA-N

Density

1.682g/cm3

Solubility

10 mm in DMSO

Flash Point

215.9°C

Index Of Refraction

1.523

PSA

69.89000

Appearance

Pale yellow semi-solid

Shelf Life

0-4°C for short term (days to weeks), or -20°C for long term (months).

Shipping

-20°C (International: -20°C)

Storage

Store at -20 °C, keep in dry and avoid sunlight.

Boiling Point

433.4°C at 760 mmHg

N-Bromoacetyl-β-alanine is a versatile ADC linker widely used in the development of antibody-drug conjugates (ADCs) for targeted cancer therapies. As an effective ADC linker, N-Bromoacetyl-β-alanine enables stable conjugation between monoclonal antibodies and potent ADC cytotoxins, ensuring precise delivery of cytotoxic payloads to tumor cells. Its unique chemical structure allows for controlled release of ADC payloads, which is critical in enhancing the therapeutic index of ADCs while minimizing off-target toxicity. In modern ADC linker design, this compound offers reliable stability under physiological conditions and optimized reactivity toward antibody residues, making it suitable for site-specific and homogeneous bioconjugation strategies. By incorporating N-Bromoacetyl-β-alanine into ADC development, researchers can design linkers that balance stability in circulation and efficient payload release within the tumor microenvironment, a fundamental aspect of successful ADC therapy.

In addition to its role as a conventional ADC linker, N-Bromoacetyl-β-alanine is highly compatible with diverse ADC cytotoxins, including microtubule inhibitors and DNA-damaging agents. This flexibility allows biochemists and pharmaceutical developers to construct a wide range of ADC payloads tailored to specific tumor types and therapeutic objectives. The linker’s chemical versatility supports conjugation methods that preserve antibody functionality and antigen-binding specificity, which is essential in maintaining ADC efficacy. Moreover, the ADC linker design using N-Bromoacetyl-β-alanine contributes to improved pharmacokinetics and biodistribution profiles, enabling higher tumor accumulation of cytotoxic payloads. Its predictable reactivity also facilitates scalable manufacturing, making it an attractive choice for both preclinical research and clinical ADC production.

From an application perspective, N-Bromoacetyl-β-alanine-based ADC linkers are increasingly employed in targeted oncology therapies, bioconjugation research, and advanced drug delivery systems. They support modular ADC architectures, allowing the incorporation of cleavable or non-cleavable linker strategies depending on the therapeutic goal. By leveraging this ADC linker, researchers can design ADC payload conjugates that exhibit high tumor specificity, efficient intracellular release, and minimized systemic toxicity.

1. Synthesis of N alpha-(tert-butoxycarbonyl)-N epsilon-[N-(bromoacetyl)-beta-alanyl]-L-lysine: its use in peptide synthesis for placing a bromoacetyl cross-linking function at any desired sequence position

J K Inman, P F Highet, N Kolodny, F A Robey Bioconjug Chem. 1991 Nov-Dec;2(6):458-63. doi: 10.1021/bc00012a014.

A new amino acid derivative, N alpha-(tert-butoxycarbonyl)-N epsilon-[N-(bromoacetyl)-beta-alanyl]-L-lysine (BBAL), has been synthesized as a reagent to be used in solid-phase peptide synthesis for introducing a side-chain bromoacetyl group at any desired position in a peptide sequence. The bromoacetyl group subsequently serves as a sulfhydryl-selective cross-linking function for the preparation of cyclic peptides, peptide conjugates, and polymers. BBAL is synthesized by condensation of N-bromoacetyl-beta-alanine with N alpha-Boc-L-lysine and is a white powder which is readily stored, weighed, and used with a peptide synthesizer, programmed for N alpha-Boc amino acid derivatives. BBAL residues are stable to final HF deprotection/cleavage. BBAL peptides can be directly coupled to other molecules or surfaces which possess free sulfhydryl groups by forming stable thioether linkages. Peptides containing both BBAL and cysteine residues can be self-coupled to produce either cyclic molecules or linear peptide polymers, also linked through thioether bonds. Products made with BBAL peptides may be characterized by amino acid analysis of acid hydrolyzates by quantification of beta-alanine, which separates from natural amino acids in suitable analytical systems. Where sulfhydryl groups on coupling partners arise from cysteine residues, S-(carboxymethyl)cysteine in acid hydrolyzates may also be assayed for this purpose. Examples are given of the use of BBAL in preparing peptide polymers and a peptide conjugate with bovine albumin to serve as immunogens or model vaccine components.

What is N-Bromoacetyl-β-alanine and how is it applied in ADC linker chemistry?

N-Bromoacetyl-β-alanine is a reactive bromoacetyl-functionalized linker that selectively reacts with thiol groups on antibodies or payloads. It provides stable thioether linkage formation for ADCs, improving conjugation efficiency and ADC stability.

9/7/2022

We are interested in which payloads can be conjugated using N-Bromoacetyl-β-alanine.

This linker is suitable for thiol-containing cytotoxins, peptides, and proteins. The β-alanine spacer offers flexibility, reducing steric hindrance and maintaining antibody activity and payload functionality.

15/12/2019

Could you explain the advantages of using N-Bromoacetyl-β-alanine in ADCs?

It forms stable thioether bonds resistant to reduction, enhancing ADC circulation stability. The short β-alanine spacer maintains appropriate payload positioning for efficient delivery to target cells.

6/6/2019

Dear team, could you kindly advise the recommended conjugation conditions?

Perform conjugation in slightly basic aqueous or organic-aqueous mixed solvents (pH 7–8) at controlled temperatures to promote selective thiol-alkylation while minimizing side reactions.

15/8/2017

Dear team, what safety measures are recommended when working with N-Bromoacetyl-β-alanine in a laboratory setting?

N-Bromoacetyl-β-alanine should be handled using standard laboratory safety procedures including gloves, goggles, and lab coats. Work in a fume hood to prevent inhalation, and store at low temperatures in sealed containers. These precautions ensure both user safety and compound integrity for subsequent bioconjugation reactions.

19/10/2017

— Dr. Peter Adams, Medicinal Chemist (UK)

N-Bromoacetyl-β-alanine displayed excellent reactivity for our thiol-targeted ADC studies.

6/6/2019

— Ms. Laura Bennett, Biochemist (USA)

High purity and consistent batch quality made N-Bromoacetyl-β-alanine a reliable reagent.

19/10/2017

— Dr. François Martin, Senior Researcher (France)

We integrated N-Bromoacetyl-β-alanine seamlessly into multi-step conjugation workflows.

15/8/2017

— Dr. Katherine Lewis, Bioconjugation Scientist (Canada)

This product helped us achieve reproducible conjugation with minimal side reactions.

9/7/2022

— Mr. Thomas Green, Chemist (Germany)

BOC Sciences provided thorough QC and documentation for N-Bromoacetyl-β-alanine, ensuring smooth ADC synthesis.

— Mr. Daniel Foster, Organic Chemist (USA)

BOC Sciences supplied N-Bromoacetyl-β-alanine with excellent consistency. Our functionalization reactions showed high conversion rates with minimal side products.

15/12/2019