Fmoc-Thi-OH is an Fmoc-protected unnatural amino acid featuring a thiophene heterocycle as the side chain. Structurally, the molecule comprises a fluorenylmethyloxycarbonyl (Fmoc) group protecting the α-amino functionality, a central alanine-derived chiral center, and a 2-thienyl group at the β-position. The thiophene ring serves as a sulfur-containing aromatic bioisostere of the phenylalanine benzene ring, offering similar electronic properties but with distinct polarizability and hydrogen-bonding characteristics.
Fmoc-Thi-OH (N-α-Fmoc-β-(2-thienyl)-L-alanine) is a standard building block for the introduction of thienylalanine into peptide sequences via Fmoc solid-phase peptide synthesis. As a useful replacement for phenylalanine (Phe), Fmoc-Thi-OH enables researchers to systematically evaluate the impact of aromatic ring substitution on peptide conformation, receptor recognition, and pharmacokinetic properties. The thiophene side chain of Fmoc-Thi-OH introduces a sulfur atom that can participate in unique electronic interactions, including π‑stacking, sulfur–aromatic interactions, and metal coordination, broadening the chemical space accessible in peptide design. Fmoc-Thi-OH is supplied with detailed characterization data and is suitable for applications ranging from academic peptide research to commercial peptide manufacturing, supported by comprehensive analytical documentation including HPLC purity and enantiomeric verification.
Product Parameters
Parameter
Specification
Product Name
Fmoc-Thi-OH
CAS Number
130309-35-2
Molecular Formula
C₂₂H₁₉NO₄S
Molecular Weight
393.46 g/mol
Appearance
White solid
Melting Point
218.5°C
Boiling Point
623.4 ± 55.0 °C (predicted)
Density
1.2174 g/cm³ (rough estimate)
Refractive Index
1.5060 (estimate)
Storage Condition
Keep in dark place,Sealed in dry,2-8°C
Product Advantages
1. Thiophene as a Phenylalanine Bioisostere
Fmoc-Thi-OH serves as a direct replacement for phenylalanine in peptide sequences, with the thiophene ring offering distinct electronic properties including enhanced polarizability and sulfur-mediated interactions. This enables SAR studies that probe the contributions of aromatic π‑systems to receptor recognition.
2. Fmoc Compatibility with Standard SPPS
The Fmoc protecting group on Fmoc-Thi-OH is fully compatible with conventional Fmoc SPPS workflows, allowing for straightforward incorporation into peptide chains using standard coupling reagents (HBTU, HATU, DIC) and deprotection protocols (20% piperidine in DMF).
3. Enhanced Proteolytic Stability
Peptides containing Fmoc-Thi-OH in place of phenylalanine often exhibit improved resistance to enzymatic degradation, extending their half-life in biological systems and enhancing therapeutic potential.
4. Versatile Replacement Strategy
The thiophene heterocycle of Fmoc-Thi-OH offers a subtle yet significant electronic modification compared to phenylalanine, making it an ideal tool for systematic SAR studies in drug discovery campaigns targeting GPCRs, ion channels, and enzyme active sites.
5. High Purity and Enantiomeric Integrity
Cosperpharm supplies Fmoc-Thi-OH with ≥99.0% HPLC purity and ≥99.5% enantiomeric purity, verified by chiral HPLC, ensuring that every batch meets the highest quality standards for demanding peptide synthesis applications.
6. Multiple Application Domains
Fmoc-Thi-OH is utilized across peptide synthesis, drug development (oncology and neurology), bioconjugation for targeted therapies, protein engineering to improve metabolic stability, and analytical chemistry as a reference standard.
FAQ
Q1: Is Fmoc-Thi-OH suitable for automated peptide synthesizers?
A: Yes. Fmoc-Thi-OH is fully compatible with automated SPPS instruments and standard Fmoc chemistry workflows. It couples efficiently using standard coupling reagents and deprotects cleanly with piperidine in DMF.
Q2: Is Fmoc-Thi-OH intended for therapeutic use?
A: No. Fmoc-Thi-OH is supplied as a research chemical and synthetic intermediate for peptide synthesis applications only. It is not intended for human consumption or therapeutic administration.
Product Quality Assurance
Cosperpharm has established a comprehensive quality assurance system for Fmoc-Thi-OH that meets the rigorous expectations of both research and commercial peptide synthesis applications:
Thorough analytical characterization. Each batch undergoes multi‑technique analytical release testing: HPLC purity (≥99.0% area%), enantiomeric purity (≥99.5% a/a, chiral HPLC), assay (acidimetric, ≥96.0%), TLC purity (≥98%), water content (Karl Fischer, ≤1.00%), melting point verification (170–180 °C), appearance verification (white to slight yellow to beige powder), identity confirmation (IR), and solubility verification in DMF. Physical property verification (density, refractive index) is conducted in accordance with established specifications.
Full batch traceability with retention samples. From raw material procurement through Fmoc protection, purification, and final packaging, every step is fully documented and traceable. Each batch receives a unique lot number with sufficient retention samples maintained in accordance with Cosperpharm quality procedures.
Stability monitoring program. Cosperpharm conducts ongoing stability studies under recommended storage conditions (15–25 °C, sealed container, dry environment). Stability summaries are available upon request to support customer quality documentation.
Documentation ready for your records. Every shipment includes a Certificate of Analysis (COA) with batch‑specific purity and characterization data, a Material Safety Data Sheet (SDS), and customs documentation for international delivery. For customers requiring additional regulatory support, Cosperpharm can provide custom quality agreements upon request.
Customer‑initiated quality audits. Qualified customers are welcome to audit Cosperpharm‘s manufacturing, quality control, and documentation facilities. Please contact our regulatory team to schedule an audit.
Contact Us
Whether you are developing a novel peptide therapeutic, optimizing a synthesis workflow, or scaling up for commercial manufacturing, Cosperpharm provides the Fmoc-Thi-OH you need with the quality and service you deserve. Reach out to our team for product specifications, pricing, or technical support — we are here to help your project succeed.
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