Production Method 1

154445-77-9

91000-69-0

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  1,1,1,3,3,3-Hexafluoro-2-propanol ;  90 min, 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 2

74-79-3

28920-43-6

91000-69-0

Reaction Conditions

Reference

Amino acid analysis by high-performance liquid chromatography with methanesulfonic acid hydrolysis and 9-fluorenylmethylchloroformate derivatization

Malmer, Marcia F.; Schroeder, Lauren Alfred, Journal of Chromatography, 1990, 514(2), 227-39

Production Method 3

74-79-3

82911-69-1

91000-69-0

Reaction Conditions

1.1 Reagents: Dicyclohexylamine Solvents: Acetone ;  4 - 5 h, rt
1.2 Reagents: Sodium carbonate Solvents: Acetonitrile ,  Water ;  pH 8, 0 - 5 °C; overnight, 5 °C → rt

Reference

Efficient procedure for the preparation of oligomer-free Nα-Fmoc amino acids

Nowshuddin, Shaik; Rao, M. N. A.; Reddy, A. Ram, Synthetic Communications, 2009, 39(11), 2022-2031

Production Method 4

74-79-3

28920-43-6

91000-69-0

Reaction Conditions

1.1 Solvents: Water ;  20 min, rt
1.2 Reagents: Amantadine ;  rt

Reference

Sensitive analysis of N-blocked amino acids using high-performance liquid chromatography with paired ion electrospray ionization mass spectrometry

Wang, Yadi; Du, Siqi; Armstrong, Daniel W., Analytical and Bioanalytical Chemistry, 2018, 410(19), 4725-4735

Production Method 5

154445-77-9

91000-69-0

1202179-48-3

Reaction Conditions

1.1 Reagents: Diisopropylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ;  1 min, rt; 1 h, rt
1.2 Reagents: Acetic anhydride Catalysts: 4-(Dimethylamino)pyridine Solvents: Dimethylformamide ;  30 min, rt
1.3 Reagents: Trifluoroacetic acid ,  Triisopropylsilane Solvents: Water ;  2 h, rt

Reference

Synthesis of an arginine tagged [Cys154-Arg180] fragment of NY-ESO-1: elimination of an undesired by-product using 'in house' resins

Harris, Paul W. R.; Brimble, Margaret A., Synthesis, 2009, (20), 3460-3466

Fmoc-Arg-OH Raw materials

• L-Arginine
• (9H-fluoren-9-yl)methyl chloroformate
• Fmoc-Arg(Pbf)-OH
• Fmoc-OSu

Fmoc-Arg-OH Preparation Products

• Fmoc-Arg-OH (91000-69-0)
• Fmoc-Arg-HMBA-Arg6-OH (1202179-48-3)

• 1. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 2. An artificial blood vessel implanted three-dimensional microsystem for modeling transvascular migration of tumor cells?
  Xue-Ying Wang,Ying Pei,Min Xie,Zi-He Jin,Ya-Shi Xiao,Yang Wang,Li-Na Zhang,Yan Li,Wei-Hua Huang Lab Chip, 2015,15, 1178-1187
• 3. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550
• 4. An apparatus for testing water by measurement of its electrical conductivity
  Analyst, 1912,37, 538-543
• 5. An apparatus for determining small amounts of alchohol in sour milk and urine
  Analyst, 1964,89, 272-275

• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Fmoc-Arg-OH (CAS No. 91000-69-0): A Critical Building Block in Peptide Synthesis and Drug Development

The Fmoc-Arg-OH (9-fluorenylmethyl carbamate-L-arginine tert-butyl ester, CAS No. 91000-69-0) is a pivotal reagent in modern chemical biology and pharmaceutical research. This compound serves as a protected amino acid derivative widely utilized in solid-phase peptide synthesis (SPPS), where the Fmoc protecting group ensures precise control over amino acid coupling during multi-step syntheses. The CAS No. 91000-69-0 uniquely identifies this compound within global chemical databases, ensuring accurate procurement and regulatory compliance across laboratories worldwide.

Recent advancements in Fmoc-based peptide synthesis have expanded the compound's applications beyond traditional SPPS. A 2023 study published in Nature Chemistry demonstrated its role in synthesizing cyclic peptides for targeted cancer therapies, leveraging the arginine residue's affinity for cell membrane interactions. The Fmoc protecting group's photolytic stability under UV light enables iterative deprotection-coupling cycles essential for constructing complex peptide architectures, such as those required for mimicking natural antimicrobial peptides.

In drug discovery pipelines, Fmoc-Arg-OH contributes to the development of bioconjugates through orthogonal deprotection strategies. Researchers at MIT recently utilized this reagent to create dual-functionalized peptides combining T-cell engagers with tumor-penetrating domains, achieving unprecedented efficacy in preclinical glioblastoma models. The compound's tert-butyl ester functionality also facilitates orthogonal protection schemes when combined with BOC or Alloc groups, enabling simultaneous modification of multiple peptide moieties during parallel synthesis campaigns.

Spectroscopic characterization confirms the compound's purity through distinct NMR signatures: the Fmoc group exhibits characteristic proton signals at δ 7.45–7.85 ppm (aromatic region), while the arginine side chain displays diagnostic resonances at δ 3.4–3.8 ppm (guanidinium protons). Mass spectrometry data (m/z 476.3 [M+H]⁺) aligns with theoretical calculations for C₂₄H₃₁N₄O₄, ensuring compositional accuracy critical for reproducible syntheses.

Cutting-edge applications now include its use in click chemistry platforms for post-synthetic functionalization. A 2024 Angewandte Chemie report detailed its integration into azide-functionalized peptides via copper-free click reactions, creating bioorthogonal handles for fluorescent labeling without disrupting biological activity. This approach has accelerated structure-function studies of GPCR-binding peptides at leading pharmaceutical companies like Vertex Pharmaceuticals.

In vaccine development, Fmoc-Arg-OH-derived sequences are being optimized as adjuvant components to enhance T-cell responses against viral epitopes. Collaborative research between Oxford University and Moderna demonstrated that arginine-rich peptides synthesized using this reagent significantly boosted mRNA vaccine immunogenicity in murine models, pointing to potential clinical applications against emerging pathogens.

Sustainability initiatives have driven innovations in its synthesis pathways, with green chemistry approaches reported by researchers at Stanford using microwave-assisted solvent-free conditions to reduce waste by ~65% compared to traditional protocols. These advancements maintain product purity (>98% HPLC) while aligning with ESG compliance requirements increasingly demanded by global regulatory bodies.

The compound's role extends into materials science through self-assembling peptide nanofiber fabrication. A recent ACS Nano study showcased its incorporation into hydrogel scaffolds with tunable mechanical properties, demonstrating potential for regenerative medicine applications such as cartilage repair and neural tissue engineering due to arginine's inherent cell adhesion promoting properties.

In diagnostic tool development, Fmoc-Arg-OH-based probes are being engineered as fluorescent sensors for intracellular pH monitoring via FRET mechanisms involving fluorogenic deprotection events. These systems provide real-time insights into lysosomal activity dynamics without requiring genetic modification of target cells.

Ongoing investigations explore its utility in PROTAC-mediated protein degradation strategies targeting oncogenic kinases. By incorporating arginine-containing ligands synthesized with this reagent into bifunctional molecules, researchers at Dana-Farber Cancer Institute achieved selective degradation of BRD4 proteins in acute myeloid leukemia models without off-target effects observed with small molecule inhibitors.

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