68262-71-5

Basic information

• Product Name: BOC-ARG(MTS)-OH CHA
• Synonyms: BOC-ARGININE(MTS)-OH CHA;BOC-ARG(MTS)-OH CHA;α-Boc-Arg(Nω-Mesitylenesulfonyl)-OH cyclohexylammonium salt ;na-T-boc-nq-mesitylenesulfonyl-*L-arginine;α-boc-arg(nω-mesitylenesulfonyl)-oh cyclohexylammonium salt;NA-T-BOC-NW-MESITYLENESULFONYL-L-ARGININEMONOCYCLOHEXYLAMMONIUMSALT;H-4-METHYL-DL-BETA-PHE-OH;Nalpha-tert-BOC-Nomega-mesitylene-sulfonyl-L-arginine salt
• CAS NO: 68262-71-5
• Molecular Formula: C₂₀H₃₂N₄O₆S
• Molecular Weight: 555.73
• Product Categories: Boc-Amino Acids and Derivative;Boc-Amino acid series;A - H;Amino Acids;Modified Amino Acids
• Mol File: 68262-71-5.mol

Chemical Properties

• Boiling Point: 714 °C at 760 mmHg
• Flash Point: 385.6 °C
• Appearance: /
• Density: 1.28±0.1 g/cm3(Predicted)
• Vapor Pressure: 2.15E-21mmHg at 25°C
• Storage Temp.: −20°C
• PKA: 3.95±0.21(Predicted)
• CAS DataBase Reference: BOC-ARG(MTS)-OH CHA(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-ARG(MTS)-OH CHA(68262-71-5)
• EPA Substance Registry System: BOC-ARG(MTS)-OH CHA(68262-71-5)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 68262-71-5(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
BOC-ARG(MTS)-OH CHA is used as a building block for peptide synthesis for its ability to protect the arginine side chain during the assembly of peptide sequences. The BOC protecting group ensures that the arginine residue remains unreactive until specifically deprotected, allowing for the controlled synthesis of complex peptides.
Used in Bioconjugation Chemistry:
In bioconjugation chemistry, BOC-ARG(MTS)-OH CHA is used as a coupling agent for the selective attachment of peptides or other molecules to thiol-containing biomolecules. The MTS group provides a reactive handle for forming stable covalent bonds with thiols, which is crucial for the preparation of bioconjugates with defined structures and functionalities.
Used in Medicinal Chemistry:
BOC-ARG(MTS)-OH CHA is utilized as a component in the design and synthesis of therapeutic agents, particularly in the development of peptide-based drugs. Its ability to be selectively attached to biomolecules allows for the creation of targeted drug delivery systems and the enhancement of drug efficacy.
Used in Biochemical Research:
In the field of biochemistry, BOC-ARG(MTS)-OH CHA is used as a tool for studying protein-protein interactions, enzyme mechanisms, and the development of biosensors. BOC-ARG(MTS)-OH CHA's reactivity with thiol groups makes it a valuable probe for investigating the role of cysteine residues in biological systems.
Overall, BOC-ARG(MTS)-OH CHA is a multifaceted chemical entity with broad applications across various scientific disciplines, particularly in the synthesis and modification of peptides and biomolecules for research and therapeutic development.

InChI:InChI=1/C20H32N4O6S.C6H13N/c1-12-10-13(2)16(14(3)11-12)31(28,29)24-18(21)22-9-7-8-15(17(25)26)23-19(27)30-20(4,5)6;7-6-4-2-1-3-5-6/h10-11,15H,7-9H2,1-6H3,(H,23,27)(H,25,26)(H3,21,22,24);6H,1-5,7H2/t15-;/m0./s1

Downstream Products

• 129720-81-6 Boc-Arg(Mts)-Pro-hexamethyleneimine 
• 129720-90-7 Boc-Arg(Mts)-Pro-cycloheptylamine 
• 129741-33-9 Boc-Arg(Mts)-Pro-cyclooctylamine 
• 129720-83-8 Boc-Arg(Mts)-Pro-p-nitroaniline 
• 129720-91-8 Z-Gly-Pro-Arg(Mts)-Pro-cycloheptylamine 
• 129720-93-0 Z-Gly-Pro-Arg(Mts)-Pro-cyclooctylamine 
• 129720-84-9 Z-Gly-Pro-Arg(Mts)-Pro-p-nitroaniline 
• 1383122-25-5 C₄₀H₄₂FN₇O₃ 
• 1383122-24-4 C₃₉H₄₀FN₇O₃ 
• 1383122-23-3 C₄₀H₄₂FN₇O₃ 
• 1383122-22-2 C₃₉H₄₀FN₇O₃ 
• 1383122-21-1 C₄₀H₄₄FN₇O₂ 

Relevant articles and documents

Enhancement of the T140-based pharmacophores leads to the development of more potent and bio-stable CXCR4 antagonists.

A CXCR4 antagonistic peptide, T140, and its bio-stable analogs, such as Ac-TE14011, were previously developed. These peptides inhibit the entry of T cell line-tropic strains of HIV-1 (X4-HIV-1) into T cells. Herein, a series of TE14011 analogs having modifications in the N-terminal region were synthesized to develop effective compounds with increased biostability. Among these analogs, 4F-benzoyl-TE14011 (TF14013) showed the strongest anti-HIV activity derived from CXCR4-antagonism, suggesting that a 4-fluorobenzoyl moiety at the N-terminus of T140 analogs constitutes a novel T140-based pharmacophore for CXCR4 antagonists. Structure-activity relationship (SAR) studies on TE14011 analogs with N(alpha)-acylation by several benzoic acid derivatives have disclosed a significant relationship between the anti-HIV activity and the Hammett constant (sigma) of substituted benzoic acids. TF14013 was found to be stable in mouse serum, but not completely stable in rat liver homogenate due to deletion of the C-terminal Arg14-NH2 from the parent peptide. This biodegradation was completely suppressed by N-alkyl-amidation at the C-terminus. Taken together, the enhancement of the T140-based pharmacophores led to development of a novel CXCR4 antagonist, 4F-benzoyl-TE14011-Me (TF14013-Me), which has very high anti-HIV activity and increased biostability.

Tumor metastasis inhibiting compounds and methods

A peptide derivative containing 1 to 20 units of peptide unit represented by the following general formula [I] or a pharmaceutically acceptable salt thereof; wherein Arg represents L- or D-arginine residue, Asp represents L-aspartic acid residue, X represents L- or D-leucine, D-isoleucine, L- or D-norleucine, L- or D-phenylalanine, D-phenylglycine or D-alanine residue, and [Z] and [Y] each represents an amino acid or a peptide residue, which may be present or absent, selected from glycine, L-serine, L-threonine, L- and D-aspartic acid, L-alanine, L- and D-glutamic acid, L-proline residues and a peptide residue constituted by the foregoing amino acid residues, and a pharmaceutical composition comprising the peptide derivative. The composition of the present invention is useful as an agent for inhibiting tumor metastasis.