N-Cbz-(S)-2-azetidinecarboxylic acid is a four-membered-ring amino-acid analog often compared with proline because the nitrogen is incorporated into the ring.

The smaller azetidine ring imposes stronger ring strain and different backbone geometry than proline, making it useful in conformational peptide and peptidomimetic SAR.

Product Information

Application Scope in Constrained Proline-Analog Design

Azetidine-2-carboxylic acid can be used to test ring-size effects, turn geometry, cis/trans amide behavior and protease recognition in peptide-like structures.

Cbz Protection and Route Compatibility

Cbz protects the ring nitrogen and is commonly removed reductively. The free carboxyl supports coupling or intermediate derivatization in a Cbz-compatible route.

Procurement and QC

Confirm CAS 25654-52-8, C12H13NO4, MW 235.24 g/mol and S configuration. Ring size and stereochemistry are essential identity attributes.

For azetidine-containing peptidomimetics, Alan Scientific can support custom peptide synthesis.

Product Documents

A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.

N-Cbz-(S)-2-azetidinecarboxylic acid MSDS

Certificates of Analysis (COAs) are batch-specific. Please contact us to request the COA for your product, and we will provide it by email.

Frequently Asked Questions

How is azetidine different from proline?

It has a four-membered ring rather than a five-membered pyrrolidine ring.

What does Cbz protect?

The ring nitrogen.

Why use an azetidine residue?

To impose a different conformational constraint and ring strain.

Related Technical Resources

Read about noncanonical amino acids

Research Use Only.