Fmoc-N-Me-Arg(pbf)-OH

• CAS: 913733-27-4
• Catalog Number: ACM913733274
• Category: Main Products
• Molecular Weight: 662.79
• Molecular Formula: C35H42N4O7S
• Synonyms: Fmoc-N-Me-Arg(Pbf)-OH
• Appearance: White to off-white powder

Case Study

Fmoc-N-Me-Arg(pbf)-OH as N-Methylated Building Block for Peptide Backbone Modification

Werner, Halina M., et al. ChemBioChem 17.8 (2016): 712-718.

Fmoc-N-Me-Arg(pbf)-OH acts as an Fmoc-protected N-methylated arginine monomer for site-specific peptide backbone modification in solid-phase peptide synthesis (SPSS), used to engineer proteolytic resistance against serine proteases such as chymotrypsin.
Synthesis & Assay Protocol: This monomer was incorporated into a 21-residue model peptide via microwave-assisted Fmoc-SPPS, replacing L-arginine at positions P4 to P2' flanking the central chymotrypsin cleavage site. Modified peptides were purified by reverse-phase HPLC, confirmed by MALDI-TOF-MS, and digested with chymotrypsin. Degradation kinetics were monitored by analytical HPLC to measure half-life changes relative to the unmodified peptide.
Performance Evaluation: N-methylation at arginine residues conferred moderate, position-dependent proteolytic protection. Enhanced stability was limited to positions directly adjacent to the scissile bond (P1, P1', P3) by disrupting specific enzyme-substrate hydrogen bonds. Unlike D-α or Aib residues, it showed no long-range protective effects, and tandem substitutions yielded additive rather than synergistic stability improvements. This monomer enables rational, minimally invasive backbone modification for designing protease-resistant peptidomimetics.

Fmoc-N-Me-Arg(pbf)-OH as a Building Block for Nα-Methylated Arginine Cell-Penetrating Peptides

Calabretta, Lindsey O., et al. Journal of Peptide Science 29.5 (2023): e3468.

Fmoc-N-Me-Arg(pbf)-OH acts as an Fmoc-protected, Pbf-sidechain-stabilized Nα-methylated arginine monomer for solid-phase peptide synthesis (SPPS), enabling streamlined preparation of methylated oligoarginine cell-penetrating peptides (CPPs) with improved membrane transport.
Synthesis & Evaluation Protocol: This monomer was used in manual SPPS (37 °C, 2.5 equiv scale) to synthesize fluorescein-labeled Me-R5 and Me-R8 peptides. After coupling, global deprotection and preparative HPLC purification were performed. Permeability was assessed via octanol-water partitioning with sodium dodecanoate, and cellular uptake was quantified by flow cytometry in HeLa cells.
Performance Evaluation: Incorporation of this building block reduced topological polar surface area (TPSA) and enhanced lipid partitioning. Methylated peptides showed 23% higher HeLa uptake for Me-R5 and 34% for Me-R8 relative to unmodified oligoarginines. Benefits were strongest at low peptide concentrations and for shorter chains. This monomer enables reliable, scalable synthesis of CPPs with boosted permeability and potential for improved metabolic stability.

Custom Q&A

What is the molecular formula of Fmoc-N-me-arg(pbf)-oh?

The molecular formula of Fmoc-N-me-arg(pbf)-oh is C35H42N4O7S.

What is the molecular weight of Fmoc-N-me-arg(pbf)-oh?

The molecular weight of Fmoc-N-me-arg(pbf)-oh is 662.8 g/mol.

What are some synonyms for Fmoc-N-me-arg(pbf)-oh?

Some synonyms for Fmoc-N-me-arg(pbf)-oh are Fmoc-N-Me-Arg(Pbf)-OH, 913733-27-4, FMOC-MEARG(PBF)-OH, and others listed in the reference.

What are the InChI and InChIKey identifiers for Fmoc-N-me-arg(pbf)-oh?

The InChI for Fmoc-N-me-arg(pbf)-oh is InChI=1S/C35H42N4O7S/c1-20-21(2)31(22(3)27-18-35(4,5)46-30(20)27)47(43,44)38-33(36)37-17-11-16-29(32(40)41)39(6)34(42)45-19-28-25-14-9-7-12-23(25)24-13-8-10-15-26(24)28/h7-10,12-15,28-29H,11,16-19H2,1-6H3,(H,40,41)(H3,36,37,38)/t29-/m0/s1, and the InChIKey is MEGKXARLCPKZHJ-LJAQVGFWSA-N.

What is the XLogP3-AA value of Fmoc-N-me-arg(pbf)-oh?

The XLogP3-AA value of Fmoc-N-me-arg(pbf)-oh is 5.3.

How many hydrogen bond donor counts does Fmoc-N-me-arg(pbf)-oh have?

Fmoc-N-me-arg(pbf)-oh has 3 hydrogen bond donor counts.

What is the topological polar surface area of Fmoc-N-me-arg(pbf)-oh?

The topological polar surface area of Fmoc-N-me-arg(pbf)-oh is 169 Ų.

How many rotatable bond counts does Fmoc-N-me-arg(pbf)-oh have?

Fmoc-N-me-arg(pbf)-oh has 12 rotatable bond counts.

What is the exact mass of Fmoc-N-me-arg(pbf)-oh?

The exact mass of Fmoc-N-me-arg(pbf)-oh is 662.27742087 g/mol.

When was Fmoc-N-me-arg(pbf)-oh last modified?

Fmoc-N-me-arg(pbf)-oh was last modified on 2023-12-30 according to the reference.