Description

Boc-beta-Hoarg(Tos)-OH (CAS No. 136271-81-3) is a high-purity, protected amino acid derivative widely utilized in peptide synthesis and pharmaceutical research. With the molecular formula C₁₉H₃₀N₄O₆S, this compound features a tert-butoxycarbonyl (Boc) protecting group and a tosyl (Tos) moiety, ensuring stability during complex synthetic procedures. Its IUPAC name, (3S)-6-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid, highlights its precise structural configuration, making it ideal for controlled modifications in peptide chains. This product is rigorously tested for purity (typically ≥95% by HPLC) and is supplied as a crystalline solid, ensuring reproducibility in research applications. Suitable for SPPS (Solid-Phase Peptide Synthesis) and solution-phase synthesis, it is a critical building block for developing novel therapeutics and biochemical probes.

Properties

• CAS Number: 136271-81-3
• Complexity: 704
• IUPAC Name: (3S)-6-[[amino-(p-tolylsulfonylamino)methylene]amino]-3-(tert-butoxycarbonylamino)hexanoic acid
• InChI: InChI=1S/C19H30N4O6S/c1-13-7-9-15(10-8-13)30(27,28)23-17(20)21-11-5-6-14(12-16(24)25)22-18(26)29-19(2,3)4/h7-10,14H,5-6,11-12H2,1-4H3,(H,22,26)(H,24,25)(H3,20,21,23)/t14-/m0/s1
• InChI Key: RYHLUZMBVLFVPG-AWEZNQCLSA-N
• Exact Mass: 442.18860586
• Molecular Formula: C19H30N4O6S
• Molecular Weight: 442.5
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(=NCCC[C@@H](CC(=O)O)NC(=O)OC(C)(C)C)N
• Topological: 169
• Monoisotopic Mass: 442.18860586
• Synonyms: 136271-81-3, Boc-beta-Hoarg(Tos)-OH, BOC-L-BETA-HOMOARGININE(TOS), Boc-|A-HoArg(Tos)-OH, N-Boc-N’-tosyl-L-beta-homoarginine, (3S)-6-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid, Boc-Nw-tosyl-L-beta-homoarginine, (3S)-6-[amino-[(4-methylphenyl)sulfonylamino]methylidene]azaniumyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate, Boc-beta-Homoarg(Tos)-OH, Boc-L-beta-HArg(Tos)-OH, (S)-3-((tert-butoxycarbonyl)amino)-6-(3-tosylguanidino)hexanoic acid, MFCD03427576, Boc-|A-homoarginine(Tos), Boc-|A-Homoarg(Tos)-OH, Boc-L-b-homoarginine(Tos), Boc-L-|A-Homo-Arg(Tos)-OH, SCHEMBL14265312, DTXSID00375806, AKOS015948690, AC-9073, CS-W011600, HY-W010884, PS-12185, Boc-beta-Homoarg(Tos)-OH, >=98.0% (TLC), F12372, (3S)-6-[(E)-{Amino[(4-methylbenzene-1-sulfonyl)amino]methylidene}amino]-3-[(tert-butoxycarbonyl)amino]hexanoic acid

Application

Boc-beta-Hoarg(Tos)-OH is primarily employed in peptide chemistry as a key intermediate for introducing homoarginine analogs into peptide sequences. Its dual-protected design (Boc and Tos groups) allows selective deprotection, enabling precise chain elongation. Researchers use it to study enzyme-substrate interactions, receptor binding, and protease resistance in modified peptides. It also serves as a precursor for synthesizing peptidomimetics and constrained peptides with enhanced bioavailability.

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