Production Method 1

71989-38-3

92954-90-0

Reaction Conditions

1.1 Reagents: Amberlyst 15 Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ;  30 min, rt

Reference

Removal of acid-labile protecting or anchoring groups in the presence of polyfluorinated alcohol: Application to solid-phase peptide synthesis

Stetsenko, D. A.; Apukhtina, V. S.; Chelobanov, B. P.; Palladino, P., Russian Journal of Bioorganic Chemistry, 2016, 42(2), 143-152

Production Method 2

71989-38-3

92954-90-0

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  2 h, rt

Reference

Synthesis and characterization of a novel ester-based nucleoamino acid for the assembly of aromatic nucleopeptides for biomedical applications

Roviello, Giovanni N.; Musumeci, Domenica; Bucci, Enrico M.; Pedone, Carlo, International Journal of Pharmaceutics, 2011, 415(1-2), 206-210

Production Method 3

60-18-4

82911-69-1

92954-90-0

Reaction Conditions

1.1 Reagents: Sodium carbonate Solvents: Water ;  pH 11, cooled
1.2 Solvents: 1,4-Dioxane ;  cooled; rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Synthesis of N'-adamantyl-N-Fmoc-O-acetyl-L-tyramine

Jiang, Jiamei; Liu, Dan; Zhu, Xiujie; Kong, Jian, Shenyang Huagong Daxue Xuebao, 2011, 25(3), 229-231

Production Method 4

82911-79-3

92954-90-0

Reaction Conditions

1.1 Reagents: N,N-Dimethylaniline ,  Aluminum chloride Solvents: Dichloromethane ;  8 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

An efficient and highly selective deprotection of N-Fmoc-α-amino acid and lipophilic N-Fmoc-dipeptide methyl esters with aluminum trichloride and N,N-dimethylaniline

Di Gioia, M. L.; Leggio, A.; Le Pera, A.; Siciliano, C.; Sindona, G.; et al, Journal of Peptide Research, 2004, 63(4), 383-387

Production Method 5

71989-38-3

92954-90-0

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ;  4 h, rt

Reference

New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: dilute HCl in fluoro alcohol

Palladino, Pasquale; Stetsenko, Dmitry A., Organic Letters, 2012, 14(24), 6346-6349

Production Method 6

71989-38-3

92954-90-0

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  3 h, rt

Reference

Total solid-phase synthesis of dehydroxy fengycin derivatives

Roses, Cristina; Camo, Cristina; Oliveras, Angel; Moll, Lluis; Lopez, Nerea; et al, Journal of Organic Chemistry, 2018, 83(24), 15297-15311

Production Method 7

60-18-4

1131148-55-4

92954-90-0

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Acetonitrile ,  Water ;  2 h, rt

Reference

Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids

Ibrahim, Tarek S.; Tala, Srinivasa R.; El-Feky, Said A.; Abdel-Samii, Zakaria K.; Katritzky, Alan R., Synlett, 2011, (14), 2013-2016

Production Method 8

82911-79-3

92954-90-0

Reaction Conditions

1.1 Reagents: N,N-Dimethylaniline ,  Aluminum chloride Solvents: Dichloromethane ;  rt
1.2 Reagents: Hydrogen ion Solvents: Water ;  rt

Reference

Alternative and chemoselective deprotection of the α-amino and carboxy functions of N-Fmoc-amino acid and N-Fmoc-dipeptide methyl esters by modulation of the molar ratio in the AlCl3/N,N-dimethylaniline reagent system

Di Gioia, Maria Luisa; Leggio, Antonella; Le Pera, Adolfo; Liguori, Angelo; Perri, Francesca; et al, European Journal of Organic Chemistry, 2004, (21), 4437-4441

Fmoc-Tyr-OH Raw materials

• L-Tyrosine
• N-Fmoc-1H-benzotriazole
• Fmoc-Tyr(tBu)-OH
• Fmoc-OSu
• (S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Fmoc-Tyr-OH Preparation Products

• Fmoc-Tyr-OH (92954-90-0)

• 1. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 2. Exchangeability of amino acid residues with similar physicochemical properties in coiled-coil interactions?
  Guiying Zhang,Maosheng Cheng,Yanni Li,Keliang Liu,Lifeng Cai Chem. Commun., 2013,49, 11086-11088
• 3. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 4. Fast-Track to Research Data Management in Experimental Material Science-Setting the Ground for Research Group Level Materials Digitalization.
  LarsBanko,AlfredLudwig
• 5. Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents
  Craig A. Kelly,David R. Rosseinsky Phys. Chem. Chem. Phys., 2001,3, 2086-2090

• 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

Comprehensive Overview of Fmoc-Tyr-OH (CAS No. 92954-90-0): Applications, Synthesis, and Industry Trends

Fmoc-Tyr-OH (CAS No. 92954-90-0), also known as N-Fmoc-L-tyrosine, is a critical building block in peptide synthesis and pharmaceutical research. This Fmoc-protected amino acid plays a pivotal role in solid-phase peptide synthesis (SPPS), enabling the efficient production of complex peptides and proteins. With the growing demand for peptide-based therapeutics, Fmoc-Tyr-OH has gained significant attention from researchers and manufacturers alike.

The compound features a fluorenylmethyloxycarbonyl (Fmoc) protecting group, which is highly stable under basic conditions but can be selectively removed under mild conditions. This property makes Fmoc-Tyr-OH particularly valuable in automated peptide synthesizers, where orthogonal protection strategies are essential. Recent advancements in peptide drug development have further highlighted the importance of high-purity Fmoc-protected amino acids like Fmoc-Tyr-OH in creating targeted therapies for conditions such as diabetes, obesity, and cancer.

From a chemical perspective, Fmoc-Tyr-OH (CAS No. 92954-90-0) demonstrates excellent solubility in common organic solvents such as DMF and DCM, making it ideal for SPPS applications. The tyrosine moiety in this compound provides a phenolic hydroxyl group that can participate in various post-translational modifications, expanding its utility in creating sophisticated peptide architectures. Many researchers are currently exploring its potential in developing peptide-based vaccines and bioconjugation strategies, particularly in the context of emerging infectious diseases.

Quality control is paramount when working with Fmoc-Tyr-OH, as impurities can significantly impact peptide synthesis outcomes. Advanced analytical techniques such as HPLC and mass spectrometry are routinely employed to verify the purity and identity of this compound. The pharmaceutical industry's increasing focus on continuous manufacturing and quality by design (QbD) principles has further elevated the standards for Fmoc-protected amino acid suppliers.

Environmental considerations are also shaping the use of Fmoc-Tyr-OH in modern laboratories. Researchers are actively developing greener synthesis protocols that reduce solvent waste and energy consumption while maintaining high yields. This aligns with the broader pharmaceutical industry's commitment to sustainable chemistry practices and the principles of green chemistry.

The global market for Fmoc-Tyr-OH (CAS No. 92954-90-0) continues to expand, driven by the growing peptide therapeutics market and increased research activity in academic institutions. Recent technological advancements in peptide synthesis equipment and automation have created new opportunities for optimizing the use of this valuable building block. As the field of precision medicine advances, the demand for high-quality Fmoc-protected amino acids is expected to rise significantly.

Storage and handling of Fmoc-Tyr-OH require careful attention to maintain its stability. The compound should be stored in a cool, dry environment, protected from light and moisture. Proper handling procedures are essential to prevent degradation and ensure consistent performance in peptide synthesis applications. These considerations are particularly important for researchers working on long peptide sequences or difficult sequences that require multiple coupling cycles.

Looking ahead, the applications of Fmoc-Tyr-OH are likely to expand into new areas of biotechnology and materials science. Researchers are exploring its potential in creating peptide-based biomaterials for tissue engineering and drug delivery systems. The compound's versatility and well-established chemistry make it a valuable tool for innovation in these emerging fields. As peptide science continues to evolve, Fmoc-Tyr-OH (CAS No. 92954-90-0) will undoubtedly remain a cornerstone of peptide research and development.

• 71989-40-7(N-Fmoc-O-benzyl-L-tyrosine)
• 119062-05-4((((9H-Fluoren-9-yl)methoxy)carbonyl)-L-aspartic acid)
• 138774-94-4(Fmoc-D-2-Nal-OH)
• 71989-38-3(Fmoc-Tyr(tBu)-OH)
• 86123-10-6(Fmoc-D-Phe-OH)
• 125700-34-7(Fmoc-[15N]Tyrosine)
• 135944-09-1(Fmoc-D-HoPhe-OH)
• 537-49-5(N-Methyl-L-tyrosine)
• 949-67-7(L-Tyrosine Ethyl Ester)
• 35661-40-6(Fmoc-Phe-OH)