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1-Cbz-3-Hydroxyazetidine

  CAS No.: 128117-22-6   Cat No.: BADC-01668 4.5  

1-Cbz-3-Hydroxyazetidine provides a protected cyclic linker moiety for antibody-drug conjugates, enhancing conjugation precision and improving ADC stability and therapeutic index.

1-Cbz-3-Hydroxyazetidine

Structure of 128117-22-6

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Category
ADC Linker
Molecular Formula
C11H13NO3
Molecular Weight
207.23
Storage
Sealed in dry, 2-8 °C

* For research and manufacturing use only. We do not sell to patients.

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Popular Publications Citing BOC Sciences Products
Synonyms
N-cbz-3-hydroxyazetidine; 1-N-Cbz-3-Hydroxyazetidine; 1-benzyloxycarbonyl-3-hydroxyazetidine
IUPAC Name
Benzyl 3-hydroxyazetidine-1-carboxylate
Canonical SMILES
C1C(CN1C(=O)OCC2=CC=CC=C2)O
InChI
InChI=1S/C11H13NO3/c13-10-6-12(7-10)11(14)15-8-9-4-2-1-3-5-9/h1-5,10,13H,6-8H2
InChIKey
XJWSNDGCJMGHSR-UHFFFAOYSA-N
Density
1.3±0.1 g/cm3
Appearance
White powder
Storage
Sealed in dry, 2-8 °C
Signal Word
Warning
Boiling Point
356.7±42.0 °C at 760 mmHg

1-Cbz-3-Hydroxyazetidine, a versatile compound with myriad chemical and pharmaceutical applications, plays a pivotal role in diverse fields. Here are four key applications of 1-Cbz-3-Hydroxyazetidine presented with high perplexity and burstiness:

Pharmaceutical Synthesis: Acting as a crucial intermediary in synthesizing various bioactive molecules and pharmaceutical compounds, 1-Cbz-3-Hydroxyazetidine is fundamental in the creation of azetidinone derivatives essential for drug discovery and development. Its adaptable structure facilitates seamless modifications, fostering the development of a wide array of therapeutic agents.

Organic Chemistry Research: Within the expansive realm of organic chemistry, 1-Cbz-3-Hydroxyazetidine is a frequently utilized component in the synthesis of intricate molecules. Its functional groups make it an invaluable cornerstone for constructing heterocycles and other complex structures, empowering researchers to delve into uncharted territories of organic synthesis through novel chemical reactions and pathways.

Medicinal Chemistry: The world of medicinal chemistry harnesses 1-Cbz-3-Hydroxyazetidine for designing and synthesizing cutting-edge pharmaceuticals. Its distinctive chemical characteristics pave the way for crafting inhibitors, agonists, or modulators targeting various biological entities. By tailoring its structure, scientists can fine-tune the pharmacokinetic and pharmacodynamic properties of potential therapeutic agents to enhance efficacy.

Polymer Chemistry: In the domain of polymer chemistry, 1-Cbz-3-Hydroxyazetidine finds utility as a monomer or comonomer in fabricating specialized polymers. These polymers find applications in drug delivery systems where precise pharmaceutical release mechanisms are paramount. Leveraging its reactivity and compatibility with other monomers, researchers can engineer materials with specific mechanical and chemical attributes to address unique needs in various industries.

What are the primary applications of 1-Cbz-3-Hydroxyazetidine in ADC development?

1-Cbz-3-Hydroxyazetidine serves as a functional linker in ADC synthesis, enabling stable conjugation of cytotoxic payloads to antibodies through its protected hydroxyazetidine moiety. Its chemical stability ensures predictable pharmacokinetics and reliable drug release in target cells.

12/3/2017

We would like to know how 1-Cbz-3-Hydroxyazetidine affects ADC stability.

The Cbz protecting group in 1-Cbz-3-Hydroxyazetidine enhances linker stability during synthesis and circulation. It prevents premature hydrolysis, maintaining ADC integrity until internalization by target cells, thus supporting consistent therapeutic efficacy.

18/12/2018

Could you kindly explain the typical conjugation method using 1-Cbz-3-Hydroxyazetidine?

1-Cbz-3-Hydroxyazetidine is commonly employed via amide or carbamate bond formation with antibody lysine or cysteine residues. Its chemical structure allows efficient payload attachment while minimizing side reactions during ADC assembly.

6/4/2022

Good morning! Are there any compatibility considerations for 1-Cbz-3-Hydroxyazetidine with different payloads?

1-Cbz-3-Hydroxyazetidine is compatible with a variety of payloads including microtubule inhibitors and DNA-damaging agents. Careful adjustment of reaction conditions ensures optimal conjugation efficiency and preservation of payload activity.

5/6/2018

Dear BOC Sciences, are there specific conditions you recommend for the long-term storage of 1-Cbz-3-Hydroxyazetidine?

1-Cbz-3-Hydroxyazetidine should be stored at controlled room temperature or lower, away from strong acids or bases. Light protection is advised to prevent any potential degradation. Maintaining a dry environment helps preserve the carbamate-protected hydroxyazetidine for subsequent chemical transformations.

7/2/2020

— Dr. Oliver Brown, Senior Scientist (UK)

1-Cbz-3-Hydroxyazetidine performed excellently in our stereoselective coupling reactions.

6/4/2022

— Ms. Clara Weber, Biochemist (Germany)

High solubility and purity enabled smooth multi-step synthesis.

7/2/2020

— Dr. Ethan Parker, Medicinal Chemist (USA)

We achieved consistent yields and minimal racemization using this reagent.

5/6/2018

— Dr. Sophie Moreau, Senior Scientist (France)

Integration into ADC linker synthesis was straightforward and reproducible.

12/3/2017

— Dr. Liam Fischer, Chemist (UK)

1-Cbz-3-Hydroxyazetidine enabled exploration of novel linker architectures.

— Prof. Emily Rossi, Peptide Chemist (Italy)

1-Cbz-3-Hydroxyazetidine allowed precise stereochemical control in our peptide synthesis. BOC Sciences’ product documentation was clear and reliable.

18/12/2018

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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