Boc-trans-3-hydroxy-L-proline (CAS 187039-57-2) is the N-Boc protected form of trans-3-hydroxy-L-proline, a chiral building block for peptide synthesis. The acid-labile Boc group is removed with TFA or HCl, so it suits Boc SPPS, solution-phase coupling, and N-terminal capping in Fmoc SPPS.

Boc-trans-3-hydroxy-L-proline is trans-3-hydroxy-L-proline with a tert-butoxycarbonyl (Boc) group on the ring nitrogen. Because Boc is removed under acid conditions, it is the natural protecting group for Boc solid-phase synthesis and solution-phase coupling, and it can be introduced as the final N-terminal residue in Fmoc synthesis. It is a hydroxyproline chiral building block for applications where stereochemical integrity matters, and is part of Hzymes' Enlicitide (MK-0616) building-block series.

Product Overview

This derivative of trans-3-hydroxy-L-proline keeps the (2S,3S) configuration of the parent compound while masking the ring nitrogen with Boc. It is used in peptide research, including hydroxyproline-containing model peptides, and in peptide manufacturing workflows.

Hzymes reports limited solubility in dichloromethane (DCM); consult the solubility data supplied with the COA when choosing a solvent.

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

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

It is a Boc-protected derivative of trans-3-hydroxy-L-proline used as a chiral building block in peptide synthesis.

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

The CAS number is 187039-57-2.

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

Its Boc group is acid-labile, so it is the natural choice for Boc SPPS and solution-phase work. In Fmoc SPPS it can be coupled as the final N-terminal residue, because piperidine does not remove Boc and the chain cannot be extended further.

How is the Boc group removed?

With acid, typically TFA in DCM or HCl in dioxane.

What should I do if it has poor solubility?

Hzymes data show limited solubility in DCM. A more polar aprotic solvent such as DMF or NMP is commonly used instead; confirm against the solubility data supplied with the COA.