183070-44-2

Basic information

• Product Name: FMOC-P-CARBOXY-PHE(OTBU)-OH
• Synonyms: FMOC-L-PHE(4-COO-TBU);FMOC-O-T-BUTYL-P-CARBOXY-L-PHENYLALANINE;FMOC-PHE(4-COOTBU)-OH;FMOC-P-CARBOXY-PHENYLALANINE(OTBU)-OH;FMOC-P-CARBOXY-PHE(OTBU)-OH;FMOC-CPH(P-OTBU)-OH;FMOC-(4-CARBOXY-T-BUTYL)-L-PHENYLALANINE;FMOC-(4-T-BUTYLOXYCARBONYL)-L-PHENYLALANINE
• CAS NO: 183070-44-2
• Molecular Formula: C₂₉H₂₉NO₆
• Molecular Weight: 487.54
• Mol File: 183070-44-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 684.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.247±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: FMOC-P-CARBOXY-PHE(OTBU)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-P-CARBOXY-PHE(OTBU)-OH(183070-44-2)
• EPA Substance Registry System: FMOC-P-CARBOXY-PHE(OTBU)-OH(183070-44-2)

Safety Data

• Hazardous Substances Data: 183070-44-2(Hazardous Substances Data)

Usage

Description

FMOC-P-CARBOXY-PHE(OTBU)-OH, also known as Fmoc-protected p-carboxyphenylalanine tert-butyl ester, is a chemical compound used in the field of peptide synthesis. It is a white powder with specific chemical properties that make it suitable for this application. The compound is characterized by its Fmoc (9-fluorenylmethoxycarbonyl) protecting group, which is commonly used in peptide synthesis to protect the amino group of amino acids during the process.

Uses

Used in Pharmaceutical Industry:
FMOC-P-CARBOXY-PHE(OTBU)-OH is used as a building block for Fmoc-based solid-phase peptide synthesis. The application reason is that it allows for the stepwise construction of peptides through the formation of amide bonds between the carboxyl group of one amino acid and the amino group of another, while the Fmoc group protects the amino group from unwanted reactions.
In the context of peptide synthesis, FMOC-P-CARBOXY-PHE(OTBU)-OH is particularly useful for the synthesis of complex peptides with specific sequences and functionalities. This is due to the versatility of the Fmoc strategy, which allows for the selective deprotection and coupling of amino acids in a controlled manner. The compound's use in this industry is driven by the need for efficient and reliable methods to produce peptides for various applications, including drug development, research, and diagnostics.

Upstream product

• 5513-40-6 benzyl N-carbobenzyloxy-L-tyrosine 
• 183070-43-1 4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid tert-butyl ester 
• 183070-42-0 4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid 
• 183070-41-9 L-N^α-Cbz-4-(O-trifluoromethanesulfonate)tyrosine benzyl ester 

Downstream Products

• 623950-10-7 4-{2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-propyl}-benzoic acid tert-butyl ester 
• 1609553-73-2 C₇₁H₈₁N₇O₁₄ 
• 327618-33-7 tert-butyl (S)-4-(2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methoxy-3-oxopropyl)benzoate 

Relevant articles and documents

Stereospecific synthesis of 4-carboxyphenylalanine and derivatives for use in Fmoc-based solid-phase peptide synthesis

Starting from N(α)-benzyloxycarbonyl-L-tyrosine(O-triflate) benzyl ester, we have prepared enantiomerically pure 4-carboxyphenylalanine and 4-methoxycarbonylphenylalanine derivatives using palladium (0) catalyzed carbonylation reactions. These unnatural amino acids were suitably protected and were used in solid-phase peptide synthesis using the Fmoc/t-butyl approach.