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(R)-(+) Azetidine-2-carboxylic acid

  CAS No.: 7729-30-8   Cat No.: BADC-01937   Purity: 97.0% 4.5  

(R)-(+) Azetidine-2-carboxylic acid is a rigid, cyclic amino acid ideal for stabilizing ADC linker frameworks. Its conformational constraints enhance spatial control in drug conjugates, making it a valuable intermediate for creating cleavable or non-cleavable linkers in site-specific bioconjugation strategies.

(R)-(+) Azetidine-2-carboxylic acid

Structure of 7729-30-8

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Category
ADC Linker
Molecular Formula
C4H7NO2
Molecular Weight
101.10

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Popular Publications Citing BOC Sciences Products
Synonyms
(R)-azetidine-2-carboxylic acid; D-Azetidine-2-carboxylic acid; (2R)-azetidin-1-ium-2-carboxylate
IUPAC Name
(2R)-azetidine-2-carboxylic acid
Canonical SMILES
C1CNC1C(=O)O
InChI
InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m1/s1
InChIKey
IADUEWIQBXOCDZ-GSVOUGTGSA-N
Density
1.275±0.06 g/cm3
Solubility
Soluble in Methanol (Slightly), Methanol (Slightly)
Melting Point
209-211°C
Appearance
White to off-white Solid
Boiling Point
242.0±33.0 °C at 760 mmHg

(R)-(+) Azetidine-2-carboxylic acid, a versatile chiral building block, finds diverse applications in various scientific domains. Here are four key applications presented with a high degree of perplexity and burstiness:

Pharmaceutical Synthesis: As a pivotal chiral intermediate, (R)-(+) Azetidine-2-carboxylic acid plays a crucial role in synthesizing an array of pharmaceutical compounds. Its intricate structure enables the generation of complex molecules essential for drug development, particularly in crafting anti-inflammatory and antiviral agents. The stereochemistry offered by this compound is indispensable in ensuring the desired therapeutic efficacy of the resulting drugs, showcasing the intricate dance of chemistry in medicine.

Peptide and Protein Chemistry: Delving into the realm of peptides and proteins, this compound acts as an unnatural amino acid analog, elevating the stability and biological activity of synthesized molecules. Incorporating (R)-(+) Azetidine-2-carboxylic acid into peptide sequences not only enhances their functionality but also aids researchers in exploring protein folding dynamics and innovating novel biomolecules with enhanced properties, illustrating the fusion of creativity and science in biomolecular design.

Asymmetric Synthesis: Organic chemistry witnesses the invaluable contribution of (R)-(+) Azetidine-2-carboxylic acid as a powerful tool for asymmetric synthesis, enabling the production of enantiomerically pure compounds. Its integration in catalytic reactions facilitates the generation of products with precise chiral configurations, a critical aspect for developing catalysts for industrial sectors and crafting chiral ligands. This synthesis journey exemplifies the meticulous artistry behind creating specific molecular shapes and configurations.

Material Science: Venturing into the realm of advanced materials, (R)-(+) Azetidine-2-carboxylic acid finds application in shaping polymers and hydrogels with unique mechanical and thermal characteristics. Its incorporation into polymer chains unlocks a realm of possibilities for creating materials tailored for specific applications, ranging from drug delivery systems to biodegradable plastics and responsive materials. This synergy of chemistry and material science heralds a new era of innovation in material engineering, blending creativity with functionality for diverse applications.

What is (R)-(+) Azetidine-2-carboxylic acid and its role in ADC linker chemistry?

(R)-(+) Azetidine-2-carboxylic acid is a cyclic amino acid used to modulate linker rigidity and conformation in ADCs. Incorporating this residue can influence ADC stability, payload orientation, and overall pharmacokinetic behavior.

17/2/2020

Could you kindly explain how (R)-(+) Azetidine-2-carboxylic acid is incorporated into linkers?

It is typically introduced via standard peptide coupling techniques into amino-functionalized linkers, enabling precise control over ADC geometry and enhancing conjugation site selectivity without affecting antibody integrity.

25/10/2017

We would like to know the benefits of using (R)-(+) Azetidine-2-carboxylic acid in ADCs.

Its rigid cyclic structure improves linker conformational stability, reduces flexibility-induced degradation, and can enhance selective release of payloads in the target cellular environment, optimizing ADC performance.

29/8/2020

Dear BOC Sciences, which solvents and conditions are recommended for its incorporation?

Conjugation is performed in polar aprotic solvents such as DMF or DMSO using carbodiimide or HATU-mediated coupling at controlled temperatures to achieve high efficiency while preserving antibody activity.

29/8/2018

Good afternoon! Which analytical documents are provided for (R)-(+) Azetidine-2-carboxylic acid to support quality assessment?

For (R)-(+) Azetidine-2-carboxylic acid, BOC Sciences provides supporting analytical documents including NMR spectra, MS data, and HPLC profiles. These documents allow researchers to verify identity and confirm structural integrity before use in synthesis or peptide modification workflows.

12/2/2017

— Dr. Alexander Schmidt, Senior Chemist (Germany)

(R)-(+) Azetidine-2-carboxylic acid demonstrated excellent stereochemical purity, critical for our ADC constructs.

29/8/2020

— Ms. Grace Wilson, Biochemist (UK)

Batch consistency of (R)-(+) Azetidine-2-carboxylic acid allowed smooth workflow integration.

12/2/2017

— Dr. Ethan Parker, Medicinal Chemist (USA)

High solubility and stability enabled efficient incorporation into our conjugation reactions.

29/8/2018

— Dr. Michael Green, Peptide Chemist (Germany)

BOC Sciences’ (R)-(+) Azetidine-2-carboxylic acid exhibited excellent optical purity, supporting our peptide synthesis workflow.

17/2/2020

— Mr. Liam Johnson, Research Scientist (Canada)

Technical support ensured optimal handling of (R)-(+) Azetidine-2-carboxylic acid, improving yield.

— Dr. Sophia Martinez, Peptide Chemist (Spain)

BOC Sciences’ (R)-(+) Azetidine-2-carboxylic acid exhibited excellent optical purity and stability. Our peptide synthesis runs were smooth, and yields improved significantly.

25/10/2017

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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