Description

(R)-N^ω-(t-Butoxycarbonyl)-N^α-(9-fluorenylmethoxycarbonyl)-α-methylornithine (CAS No. 171860-40-5) is a high-purity, protected amino acid derivative designed for peptide synthesis and biochemical research. This compound features a molecular formula of C₂₆H₃₂N₂O₆ and is characterized by its dual protection with tert-butoxycarbonyl (Boc) and fluorenylmethoxycarbonyl (Fmoc) groups, ensuring selective deprotection during solid-phase peptide synthesis (SPPS). The α-methyl substitution introduces steric constraints, making it valuable for studying peptide conformation and stability. Ideal for researchers in medicinal chemistry and drug discovery, this product is rigorously tested for purity (≥95% by HPLC) and is supplied as a white to off-white crystalline powder. Store at -20°C under inert conditions to maintain stability.

Properties

• CAS Number: 171860-40-5
• Complexity: 713
• IUPAC Name: (2R)-5-(tert-butoxycarbonylamino)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-pentanoic acid
• InChI: InChI=1S/C26H32N2O6/c1-25(2,3)34-23(31)27-15-9-14-26(4,22(29)30)28-24(32)33-16-21-19-12-7-5-10-17(19)18-11-6-8-13-20(18)21/h5-8,10-13,21H,9,14-16H2,1-4H3,(H,27,31)(H,28,32)(H,29,30)/t26-/m1/s1
• InChI Key: HUGFTODLQPYAOF-AREMUKBSSA-N
• Exact Mass: 468.22603674
• Molecular Formula: C26H32N2O6
• Molecular Weight: 468.5
• SMILES: C[C@@](CCCNC(=O)OC(C)(C)C)(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Topological: 114
• Monoisotopic Mass: 468.22603674
• Synonyms: 171860-40-5, (R)-Nomega-(t-Butoxycarbonyl)-Nalpha-(9-fluorenylmethoxycarbonyl)-alpha-methylornithin, 691-378-1, Fmoc-Alpha-Me-D-Orn(Boc)-OH, (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid, (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)-2-methylpentanoic acid, (R)-Na-Fmoc-NW-Boc-alpha-Methylornithine, MFCD17019259, FMoc–Me-D-Orn(Boc)-OH, Fmoc-beta-Me-D-Orn(Boc)-OH, AKOS030212535, AT30755, (2r)-5-(tert-butoxycarbonylamino)-2-(9h-fluoren-9-ylmethoxycarbon Ylamino)-2-methyl-pentanoic Acid, (2R)-2-((((9H-FLUOREN-9-YL)METHOXY)CARBONYL)AMINO)-5-((TERT-BUTOXYCARBONYL)AMINO)-2-METHYLPENTANOIC ACID

Application

This compound is widely used in peptide synthesis, particularly for introducing α-methylornithine residues into peptide chains to modulate backbone flexibility and proteolytic resistance. It serves as a key intermediate in the development of constrained peptidomimetics and enzyme inhibitors. Researchers also employ it in the study of structure-activity relationships (SAR) due to its stereospecific (R)-configuration. Its dual Boc/Fmoc protection allows for orthogonal deprotection strategies in multi-step syntheses.

Safety and Hazards

GHS Hazard Statements

• Not Classified
• Reported as not meeting GHS hazard criteria by 1 of 1 companies. For more detailed information, please visit ECHA C&L website.

Hazard Classes and Categories

• Not Classified

If you are interested or have any questions, please contact us at support@atomfair.com

Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.