Product Overview

Cbz-trans-3-hydroxy-L-proline is the N-benzyloxycarbonyl (Cbz/Z)-protected derivative of trans-3-hydroxy-L-proline. Also known as a Cbz protected hydroxyproline building block, it is designed for use in complex peptide synthesis and organic synthesis where selective amino-group protection is required.

As a benzyloxycarbonyl amino acid, Cbz-trans-3-hydroxy-L-proline combines a protected amino group with a free side-chain hydroxyl group. This structural configuration provides useful flexibility for selective functionalization and orthogonal protecting group peptide strategies.

The product can be used in solid phase peptide synthesis (SPPS) and solution phase peptide synthesis, particularly in synthetic routes involving hydroxyproline-containing peptides, natural products, pharmaceutical intermediates, and other structurally complex molecules.

Its Cbz group can be removed through hydrogenolysis deprotection of Cbz, typically using Pd/C-catalyzed hydrogenation, providing a practical route for downstream amino-group deprotection.

Key Features

Cbz-Protected Hydroxyproline Building Block

The Cbz group effectively protects the amino functionality while leaving the side-chain hydroxyl group available for further functionalization. This makes the product a useful solid phase peptide synthesis building block for incorporating hydroxyproline structures into peptide sequences.

Orthogonal Protection Strategy

The combination of Cbz-protected amino functionality and a free hydroxyl group provide flexibility in multi-step synthesis. It can be incorporated into synthetic routes requiring Cbz/Fmoc orthogonal protection, depending on the overall protecting-group strategy and reaction conditions.

Practical Cbz Deprotection

The Cbz group can be removed by Pd catalyzed Cbz removal, most commonly through catalytic hydrogenation using Pd/C. Acidic systems such as HBr/AcOH can also be considered depending on the requirements of the synthetic route.

This provides a practical hydrogenolysis deprotection Cbz option for downstream synthesis.

Favorable Crystallinity and Purification

Compared with the corresponding unprotected amino acid, the protected derivative offers favorable crystallization and handling characteristics, facilitating isolation and purification during synthetic workflows.

Consistent Quality for Research and Development

Controlled manufacturing and purification processes support reliable quality and batch-to-batch consistency, making the product suitable for peptide research, pharmaceutical intermediate development, and other demanding synthetic applications.

Applications

Solid-Phase Peptide Synthesis

Cbz-trans-3-hydroxy-L-proline can be used as a solid phase peptide synthesis building block for introducing a trans-3-hydroxyproline motif into peptide sequences.

Its protected amino group and free hydroxyl functionality can provide additional flexibility when designing selective coupling and deprotection sequences.

Note: Cbz-trans-3-hydroxy-L-proline is a Cbz-protected amino acid and should not be considered equivalent to an Fmoc-protected amino acid. Compatibility with a specific SPPS strategy should be evaluated based on the selected protecting-group system.

Solution-Phase Peptide Synthesis

The product is also applicable to solution phase peptide synthesis Cbz strategies, particularly where Cbz protection is preferred for controlling amino-group reactivity during fragment synthesis and coupling.

Natural Product and Antibiotic Synthesis

Cbz-trans-3-hydroxy-L-proline can serve as a synthetic building block for hydroxy-L-proline-containing natural products, antibiotics, and their analogues, especially in routes requiring selective protection of the amino group.

Pharmaceutical and Peptide Intermediate Synthesis

The product can be incorporated into the synthesis of structurally complex pharmaceutical intermediates and peptide-based molecules where controlled amino-group protection and downstream deprotection are important.

Functional Peptide Materials

Hydroxyproline-containing structures can contribute to specific conformational and self-assembly properties. Cbz-trans-3-hydroxy-L-proline may therefore be used as an intermediate for developing functional peptide materials and related biomolecular structures.

Customer Case

University Organic Synthesis Laboratory — Total Synthesis of a Marine Alkaloid

A university organic synthesis laboratory encountered significant polymerization and purification problems when using the corresponding unprotected amino acid in the total synthesis of a marine alkaloid.

After switching to Cbz-trans-3-hydroxy-L-proline, the team improved the coupling reaction yield from 60% to 85%. The improved reaction performance also reduced purification time by approximately two weeks, enabling successful gram-scale preparation of the target natural product.

The case demonstrates how an appropriately Cbz protected amino acid can help improve reaction control and purification efficiency in challenging multi-step synthesis.

FAQ

Q1. How is the Cbz protecting group removed?

The Cbz group is commonly removed through catalytic hydrogenation. Pd/C-catalyzed Cbz removal is one of the most widely used approaches and can be performed under atmospheric or elevated hydrogen pressure depending on the synthetic system.

Acidic conditions such as HBr in acetic acid or other suitable reagents may also be used depending on the substrate and overall synthesis route.

Q2. What is Z-trans-3-Hyp-OH?

Z-trans-3-Hyp-OH is an alternative notation for the Cbz-protected form of trans-3-hydroxy-L-proline. In this notation, Z refers to the benzyloxycarbonyl (Cbz) protecting group, while Hyp refers to hydroxyproline.

Q3. Is the side-chain hydroxyl group protected?

No. Cbz-trans-3-hydroxy-L-proline contains a free side-chain hydroxyl group. The Cbz group protects the amino functionality, while the hydroxyl group remains available for further functionalization.

If protection of both the amino and hydroxyl groups is required, customized derivatives may be available through custom protected amino acid synthesis.

Q4. Can you provide custom protected amino acids?

Yes. For projects requiring specific protecting-group combinations, derivatives, or synthesis specifications, our team can discuss custom protected amino acid synthesis and related development requirements.

Q5. Do you supply Cbz-protected amino acids for commercial projects?

As a Cbz protected amino acid supplier, we can support research and development projects as well as larger-scale sourcing requirements. For pharmaceutical and commercial applications, product specifications, scale, quality requirements, and documentation can be discussed with our technical and commercial teams.

Q6. Can Cbz-trans-3-hydroxy-L-proline be used with Fmoc chemistry?

The product itself is Cbz-protected rather than Fmoc-protected. However, Cbz and Fmoc can form part of an orthogonal protection strategy when appropriately designed. The suitability depends on the specific SPPS or solution-phase synthesis route and its deprotection conditions.

Q7. Is this product the same as 4-hydroxy-L-proline?

No. Cbz-trans-3-hydroxy-L-proline is structurally different from 4-hydroxy-L-proline (4-hydroxyproline) because the hydroxyl group is located at a different position on the proline ring. These compounds should not be treated as interchangeable building blocks.