Boc-L-Orn(4S-OTIPS, 5-Z)-OH

Boc-L-Orn(4S-OTIPS, 5-Z)-OH is a Boc-protected L-ornithine derivative bearing an OTIPS-protected side-chain at the 4-position and a Z-configured substituent at the 5-position, making it a stereochemically defined, protected amino acid building block for peptide assembly. The combination of a stable Boc N-terminus and a sterically robust OTIPS group supports controlled coupling and downstream functional-group tolerance during multistep synthesis, while the defined Z geometry enables consistent incorporation into sequence-defined intermediates and peptides.

1. Fmoc-Free Peptide Building

Boc-L-Orn(4S-OTIPS, 5-Z)-OH is used as an amino acid building block in protected-amino-acid peptide synthesis workflows where Boc-based strategies are preferred, including segment condensation and custom peptide manufacturing research. The Boc group provides a protected N-terminus for stepwise assembly, while the OTIPS side-chain protection helps maintain side-chain integrity through coupling and deprotection cycles. Researchers commonly select this derivative when they need a stereodefined ornithine scaffold with a protected side chain that can be carried through to later stages for selective unveiling or further derivatization.

2. Oriented Side-Chain Functionalization

Boc-L-Orn(4S-OTIPS, 5-Z)-OH supports downstream development of ornithine-containing peptide intermediates where later side-chain modification is required. The OTIPS-protected functional handle at the 4-position is particularly useful for controlling when the side chain becomes available for subsequent transformations after peptide assembly, enabling a planned sequence of protection/deprotection and derivatization steps. Synthetic teams use this kind of stereochemically defined, protected amino acid derivative to prepare peptide fragments that preserve geometry and stereochemical information until the point of functionalization.

3. Stereodefined Peptidomimetic Intermediates

Boc-L-Orn(4S-OTIPS, 5-Z)-OH is employed in medicinal chemistry and chemical biology programs to construct stereodefined peptidomimetic scaffolds and peptide-based intermediates that require a specific 5-Z arrangement and a protected ornithine-like side chain. The defined stereochemistry and robust protection pattern help reduce variability during iterative synthesis and purification, which is valuable when building libraries of sequence- or stereoisomer-specific analogs. Teams developing structure-activity relationship (SAR) series often rely on such protected, geometry-controlled amino acid derivatives to ensure that the intended stereochemical motif is maintained through the synthetic route.

4. Protected Amino Acid Intermediate Supply

Boc-L-Orn(4S-OTIPS, 5-Z)-OH is also used as a pharmaceutical intermediate-grade building block for downstream synthesis of ornithine-derived protected fragments and specialized peptide reagents. Process development groups value the pre-installed protection pattern because it streamlines route design for producing consistent intermediates that can be carried into later coupling, fragment assembly, or selective deprotection steps. This makes the compound relevant to contract synthesis and internal development workflows that require reproducible protected amino acid inputs for complex, stereochemically defined targets.

1. Investigating Potential Interactions Between Neurohypophyseal Peptides, their Drug Analogs, and Coagulation Factor VIII

2. cRGD-functionalized, DOX-conjugated, and 64Cu-labeled superparamagnetic iron oxide nanoparticles for targeted anticancer drug delivery and PET/MR imaging

3. P-selectin and Complement’s Role in a Neonatal Model of Germinal Matrix Hemorrhage-Induced Secondary Injury

4. Extended exenatide administration enhances lipid metabolism and exacerbates pancreatic injury in mice on a high fat, high carbohydrate diet

5. C-Peptide replacement therapy and sensory nerve function in type 1 diabetic neuropathy