Ac-Arg-NH2

Ac-Arg-NH2 is an N-acetylated L-arginine amide derivative in which the α-amino group is acylated with an acetyl group (Ac) and the α-carboxyl group is converted to a primary carboxamide (-NH2), yielding a guanidinium-bearing amino acid amide. The arginine side chain contains a strongly basic guanidinium functionality that can form salt-like interactions and hydrogen bonds, while the molecule retains an N-acetylated backbone with a terminal carboxamide that modulates polarity and hydrogen-bonding capacity relative to the free amino acid. This compound is used as a peptide-related building block and substrate analogue in peptide synthesis and structure-activity or binding studies, where the arginine guanidinium group and the amide-modified C-terminus provide a defined chemical handle for studying side-chain recognition and amide-level interactions.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27320

CAS No:64365-27-1

Synonyms/Alias:H-P-FLUORO-DL-PHE-OMEHCL;64282-12-8;4-Fluoro-DL-phenylalaninemethylesterhydrochloride;methyl2-amino-3-(4-fluorophenyl)propanoatehydrochloride;SCHEMBL3498946;CTK8F5952;H-p-Fluoro-DL-Phe-OMe.HCl;H-P-FLUORO-DL-PHE-OMEHCL;MolPort-020-004-769;7216AH;KM0839;NSC523088;MCULE-1562203633;NSC-523088;AM001912;FT-0698747;3B3-064405

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M.F/Formula
C10H13ClFNO2
M.W/Mr.
215.26

Ac-Arg-NH2 is an N-acetylated L-arginine amide (Ac-Arg-NH2), featuring a terminal carboxamide that preserves the side-chain guanidinium functionality characteristic of arginine. This neutral, peptide-like building block is widely used as a defined substrate or reference fragment in peptide chemistry and chemical biology workflows where an arginine residue must be presented in an amide context rather than as a free carboxylate. The acetylated N-terminus and amide C-terminus make it particularly useful for studying or benchmarking reactions that depend on end-group identity and local peptide environment.

1. Peptide Substrate Studies

Ac-Arg-NH2 is used as a short, well-defined arginine-containing peptide substrate for evaluating peptide bond recognition and end-group effects in enzymology and protein chemistry. Researchers commonly employ this type of arginine amide fragment to probe how N-acetylation and C-terminal amidation influence processing by proteases or peptidases that discriminate between termini. Because the arginine side chain remains in its guanidinium form, the compound provides a realistic charge and hydrogen-bonding pattern for assays that rely on arginine-specific interactions, while the amide terminus helps model peptide-like substrates more closely than free amino acid standards.

2. Bioconjugation and Linker Design

Ac-Arg-NH2 serves as a practical arginine-containing building block for constructing peptide-based linkers and conjugation reagents where a terminal amide and N-acetyl cap are required for stability and defined structure. In chemical biology and biomaterials development, scientists often incorporate arginine residues to support electrostatic interactions with negatively charged biomolecules or surfaces, and the guanidinium group provides a strong, persistent cationic handle. The N-acetylated, C-amidated format also helps maintain a peptide-like backbone environment that can improve reproducibility when comparing conjugates, immobilized peptides, or binding constructs across experiments.

3. Analytical Reference Standard

Ac-Arg-NH2 is frequently used as an analytical reference compound in LC-MS and related characterization workflows that require a defined arginine-containing peptide fragment. Laboratories use it to confirm retention behavior, ionization patterns, and fragmentation features for arginine amide species, and to support method development for peptide analysis where end-group identity (acetylated N-terminus and amidated C-terminus) matters. As a chemically stable, low-complexity standard, it is also useful for calibrating workflows that quantify or qualify peptide-like analytes containing arginine motifs, including routine quality checks during peptide synthesis and purification development.

4. Pharmaceutical Intermediate Building Block

Ac-Arg-NH2 is used in pharmaceutical intermediate development and custom peptide manufacturing research as a protected/defined arginine fragment precursor for assembling larger peptide structures or for generating arginine-containing intermediates with controlled termini. The acetylated N-terminus and C-terminal amide provide a ready-made end-group pattern that can be carried forward into downstream coupling or fragment condensation strategies. This makes Ac-Arg-NH2 a convenient building block when a specific arginine motif must be introduced with peptide-like terminal functionality, supporting consistent synthesis planning for research-scale libraries and process development batches.

Size
1 g;5 g;
InChI
1S/C10H12FNO2.ClH/c1-14-10(13)9(12)6-7-2-4-8(11)5-3-7;/h2-5,9H,6,12H2,1H3;1H
InChI Key
FHEHCZJLZDLUAW-UHFFFAOYSA-N
Canonical SMILES
COC(=O)C(CC1=CC=C(C=C1)F)N.Cl

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