Introduction to Fmoc-Trp(Boc)-OH
Fmoc-Trp(Boc)-OH, also known by its CAS number 143824-78-6, is a vital chemical compound used extensively in the field of peptide synthesis. This compound, with its full chemical name (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid, is a derivative of L-tryptophan, a naturally occurring amino acid. The compound is protected with both Fmoc (9-fluorenylmethoxycarbonyl) and Boc (tert-butoxycarbonyl) groups, which are essential for its role in solid-phase peptide synthesis (SPPS).
Chemical Properties and Structure
Fmoc-Trp(Boc)-OH is characterized by its white to off-white crystalline powder appearance. It has a molecular formula of C31H30N2O6 and a molecular weight of 526.58 g/mol. The compound's melting point is approximately 97°C, and it is sensitive to moisture, requiring storage at 2-8°C to maintain its stability. The presence of the Fmoc and Boc protecting groups allows for controlled deprotection during peptide synthesis, making it a versatile intermediate.
Applications in Peptide Synthesis
Fmoc-Trp(Boc)-OH is primarily used in the synthesis of peptides containing tryptophan. The use of this N-in-Boc protected derivative overcomes many challenges associated with the preparation of Trp-containing peptides by Fmoc SPPS. Upon cleavage with trifluoroacetic acid (TFA), it generates an N-in-carboxy indole, which protects the tryptophan from alkylation and sulfonation. This protection is crucial for the successful synthesis of complex peptides, including analogs of glucagon-like peptide-1 (GLP-1), which are used in the treatment of type 2 diabetes.
Synthesis and Production
The synthesis of Fmoc-Trp(Boc)-OH involves several steps, starting from L-tryptophan. The process typically includes esterification, amidation, and protection with Boc and Fmoc groups. The compound is then hydrolyzed to yield the final product. NINGBO INNO PHARMCHEM CO.,LTD., as a leading manufacturer in China, specializes in the production of Fmoc-Trp(Boc)-OH, ensuring high purity and quality for use in pharmaceutical applications.
Safety and Handling
Handling Fmoc-Trp(Boc)-OH requires adherence to safety protocols due to its potential to cause skin and eye irritation. It is classified under hazard codes Xi and N, indicating its irritant and environmental hazard properties. Proper protective equipment, such as gloves and eye protection, should be worn when handling this compound. Additionally, it should be stored in a cool, dry place to prevent degradation.
Market and Supply
As a supplier in China, NINGBO INNO PHARMCHEM CO.,LTD. plays a significant role in the global supply of Fmoc-Trp(Boc)-OH. The company's commitment to quality and innovation ensures that researchers and pharmaceutical companies have access to this essential intermediate. The market demand for Fmoc-Trp(Boc)-OH continues to grow, driven by its critical role in peptide synthesis and drug development.
Future Prospects and Research
Ongoing research into Fmoc-Trp(Boc)-OH focuses on improving its synthesis methods and exploring new applications. The compound's role in the development of peptide-based therapeutics is particularly promising, with potential applications in treating various diseases beyond diabetes. As a manufacturer in China, NINGBO INNO PHARMCHEM CO.,LTD. is at the forefront of these advancements, continuously working to enhance the compound's utility and efficiency.
Conclusion
Fmoc-Trp(Boc)-OH is a cornerstone in the field of peptide synthesis, offering a reliable method for incorporating tryptophan into peptides. Its unique chemical properties and protective groups make it an indispensable tool for researchers and pharmaceutical companies. NINGBO INNO PHARMCHEM CO.,LTD. remains dedicated to providing high-quality Fmoc-Trp(Boc)-OH, supporting the ongoing development of innovative peptide-based therapies.
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