Product Overview

Boc-trans-3-hydroxy-L-proline, CAS No. 187039-57-2, molecular formula C₁₀H₁₇NO₅, and molecular weight 231.25 g/mol, is a protected hydroxyproline derivative widely used as a building block in peptide synthesis.

Also known as Boc protected hydroxyproline or tert-butyloxycarbonyl hydroxyproline, this compound features a Boc-protected amino group and a free carboxyl group, providing a practical protection strategy for the synthesis of hydroxyproline-containing peptides.

As a Boc SPPS building block, Boc-trans-3-hydroxy-L-proline is particularly useful in Fmoc-based solid-phase peptide synthesis (SPPS) and related peptide manufacturing workflows. Its protection profile provides useful orthogonality between the Boc and Fmoc protecting groups, making it suitable for building complex peptide sequences.

The combination of high purity, good stereochemical stability, and controlled impurity levels makes this hydroxyproline chiral building block suitable for pharmaceutical peptide synthesis, research applications, and process development.

Key Features

Fmoc-SPPS Compatible

Boc-trans-3-hydroxy-L-proline is designed for use in Fmoc-based SPPS. The Boc protecting group remains stable under typical piperidine-mediated Fmoc deprotection conditions and can be removed under acidic conditions.

This hydroxyproline Boc Fmoc orthogonal protection strategy enables selective manipulation of different functional groups during multi-step peptide synthesis.

For Boc-Hyp-OH peptide synthesis, the protected hydroxyproline structure provides a convenient route for incorporating hydroxyproline residues into target peptide sequences.

Low Racemization Risk

Under commonly used peptide coupling conditions, such as DIC/HOBt-mediated activation, the α-chiral center demonstrates good stereochemical stability, helping minimize unwanted racemization during peptide synthesis.

This makes Boc-trans-3-hydroxy-L-proline a useful hydroxyproline chiral building block for applications where stereochemical integrity is critical.

High-Purity Quality Control

Strict quality control helps maintain a single maximum impurity below 0.5% and total impurities below 1.0%, supporting demanding peptide synthesis and pharmaceutical manufacturing applications.

Our quality system is designed to provide consistent raw material performance for customers seeking a reliable Boc amino acid supplier for laboratory, process development, and manufacturing applications.

Good Organic Solvent Compatibility

The Boc protecting group increases the compound's lipophilicity and supports practical handling in commonly used organic solvents such as DMF and DCM, depending on the specific formulation and process conditions.

This property can be beneficial in both solid-phase and solution phase peptide synthesis Boc workflows.

Applications

Peptide Drug Synthesis

Boc-trans-3-hydroxy-L-proline can be used as a building block for the synthesis of hydroxyproline-containing peptide APIs and key intermediates, including peptide sequences associated with GLP-1 receptor agonists such as liraglutide and semaglutide.

Its controlled stereochemistry and orthogonal protection strategy make it suitable for complex peptide synthesis workflows.

Collagen Peptide Synthesis

Hydroxyproline is an important amino acid component of collagen-related peptide sequences. Boc-trans-3-hydroxy-L-proline can therefore be used as a protected building block in collagen peptide synthesis, peptide research, and the preparation of hydroxyproline-containing model peptides.

Diagnostic Reagent Development

Boc-trans-3-hydroxy-L-proline can be incorporated into peptides containing specific functional or labeling sites for the development of fluorescent peptide probes and diagnostic reagents.

Cosmetic Peptide Development

It can also be used as a synthetic building block for developing functional and anti-aging peptide ingredients, including modified peptide sequences for cosmetic research and formulation development.

Customer Case

Large Generic Pharmaceutical Manufacturer

A large pharmaceutical manufacturer used Boc-trans-3-hydroxy-L-proline in the process scale-up of a peptide API for a glucose-lowering drug.

The customer's previous supplier experienced significant batch-to-batch variation in moisture content, making it difficult to maintain consistent reaction endpoints during the coupling process.

After switching to our Boc protected hydroxyproline, moisture content was consistently controlled below 0.3%, while reaction conversion remained above 99%.

The improved raw material consistency contributed to an approximately 5% increase in API batch yield and generated annual cost savings of hundreds of thousands of RMB.

This case demonstrates the importance of consistent raw material quality for peptide API process development and scale-up.

FAQ

Q1: What is Boc-trans-3-hydroxy-L-proline?

Boc-trans-3-hydroxy-L-proline is a Boc-protected derivative of trans-3-hydroxy-L-proline used as a chiral building block in peptide synthesis. It is also referred to as Boc protected hydroxyproline or tert-butyloxycarbonyl hydroxyproline.

Q2: What is the CAS number of Boc-trans-3-hydroxy-L-proline?

The Boc-trans-3-hydroxy-L-proline CAS number is 187039-57-2.

Q3: Is Boc-trans-3-hydroxy-L-proline suitable for Fmoc SPPS?

Yes. Boc-trans-3-hydroxy-L-proline is compatible with Fmoc-based solid-phase peptide synthesis (SPPS). The Boc and Fmoc protection strategies offer useful orthogonality for selective functional group manipulation during peptide assembly.

Q4: How is the Boc protecting group removed?

Boc groups are generally removed under acidic conditions, commonly using TFA. Depending on the overall synthetic strategy, stronger acid systems such as HF may be used for specific deprotection and cleavage protocols. The appropriate conditions should be selected according to the peptide sequence and protecting-group strategy.

Q5: What should I do if Boc-trans-3-hydroxy-L-proline has poor solubility?

Boc-trans-3-hydroxy-L-proline has limited solubility in DCM. DMF or DMSO can be used as co-solvents to improve dissolution. In some process conditions, a small amount of N-methylmorpholine (NMM) may also be used to facilitate dissolution through salt formation.

The optimal solvent system should be determined according to the specific coupling chemistry and process requirements.

Q6: Do you provide residual solvent testing data?

Yes. We provide a detailed Certificate of Analysis (CoA) with relevant residual solvent data, including Class 2 solvents such as DMF, to support pharmaceutical manufacturing and quality assessment requirements.

Q7: Can you supply Boc amino acids for pharmaceutical manufacturing?

Yes. As a Boc amino acid GMP manufacturer and supplier, Hzymes Biotech provides protected amino acid building blocks with controlled purity and quality specifications for peptide synthesis, process development, and pharmaceutical manufacturing applications.