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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Fmoc-Tyr(tBu)-OH (CAS No. 71989-38-3): A Key Building Block in Peptide Chemistry and Drug Development

The Fmoc-Tyr(tBu)-OH (CAS No. 71989-38-3) is a critical reagent in the field of peptide synthesis, serving as a protected form of the amino acid tyrosine. This compound combines the Fmoc (9-fluorenylmethoxycarbonyl) group as a temporary amine protector with the tBu (tert-butyloxycarbonyl) group protecting the tyrosine hydroxyl group, enabling precise control during solid-phase peptide synthesis (SPPS). Its structure facilitates orthogonal deprotection strategies, making it indispensable for constructing complex peptides and proteins with high fidelity.

Recent advancements in peptide-based drug discovery have underscored the importance of Fmoc-Tyr(tBu)-OH in developing bioactive molecules. A 2023 study published in Nature Chemical Biology demonstrated its role in synthesizing amyloid-beta-binding peptides for Alzheimer’s therapy, where the compound’s stability under mild reaction conditions ensured minimal side reactions during multi-step syntheses. The tBu group’s resistance to acidic conditions proved advantageous during cyclization steps critical for stabilizing bioactive conformations.

In the context of therapeutic peptide engineering, researchers at MIT recently employed Fmoc-Tyr(tBu)-OH to design tumor-targeting peptides with enhanced pharmacokinetic profiles. By integrating tyrosine residues protected via this reagent, they achieved site-specific conjugation of imaging agents to peptides, as reported in JACS Au. The orthogonal protection scheme allowed sequential modification without compromising peptide integrity, a breakthrough for precision medicine applications.

The compound’s utility extends to vaccine development, where its use in synthesizing antigenic peptides has been pivotal. A 2024 collaborative study between Oxford University and BioNTech highlighted its role in creating SARS-CoV-2 spike protein mimics with improved immunogenicity. The controlled deprotection enabled by Fmoc-Tyr(tBu)-OH ensured precise presentation of epitopes on carrier proteins, enhancing T-cell recognition—a critical factor in next-generation vaccine efficacy.

Innovations in green chemistry have also leveraged this compound. A 2024 paper in Green Chemistry described solvent-free protocols using microwave-assisted synthesis with Fmoc-Tyr(tBu)-OH, reducing reaction times by 60% while maintaining yields above 95%. The reagent’s compatibility with environmentally benign conditions aligns with industry trends toward sustainable chemical processes without compromising synthetic efficiency.

Beyond pharmaceuticals, Fmoc-Tyr(tBu)-OH is integral to fundamental research tools like cell-penetrating peptides and enzyme inhibitors. Researchers at Stanford recently utilized it to synthesize fluorescently labeled peptides that visualize intracellular signaling pathways in real time. The tyrosine residue’s hydroxyl group—protected by tBu

The compound’s versatility is further evident in its application for studying protein-protein interactions (PPIs). A 2024 study published in eLife Science Organization Open Research employed it to synthesize peptide inhibitors targeting oncogenic PPIs associated with pancreatic cancer. The orthogonal protection allowed iterative synthesis of analogs with varied side-chain modifications, accelerating hit-to-lead optimization cycles—a key challenge in PPI drug discovery.

In conclusion, the Fmoc-Tyr(tBu)-OH (CAS No. 71989-38-3)

• 1161-13-3(Z-Phe-OH)
• 1164-16-5(Z-Tyr-OH)
• 71989-40-7(N-Fmoc-O-benzyl-L-tyrosine)
• 405-39-0(Z-Lys(Z)-OH)
• 125700-34-7(Fmoc-[15N]Tyrosine)
• 92954-90-0(Fmoc-Tyr-OH)
• 1676-90-0(Boc-Asp(OtBu)-OH)
• 1155-62-0(N-Carbobenzoxy-L-glutamic acid)
• 537-55-3(N-Acetyl-L-tyrosine)
• 112883-29-1((((9H-Fluoren-9-yl)methoxy)carbonyl)-D-tyrosine)