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
• Article Data: 2

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

General Description

BOC-ARG(MTS)-OH CHA is a chemical compound that contains the BOC (tert-butyloxycarbonyl) protecting group, as well as the amino acid arginine modified with a thiol-reactive MTS (2-sulfonatoethyl)maleimide group. BOC-ARG(MTS)-OH CHA is commonly used in peptide synthesis and bioconjugation chemistry. The BOC protecting group helps to prevent unwanted side reactions during peptide synthesis, while the MTS group allows for selective and efficient attachment of the arginine residue to thiol-containing biomolecules. Overall, BOC-ARG(MTS)-OH CHA is a versatile compound with applications in the fields of medicinal chemistry and biochemistry.

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

• 905593-25-1 {4-(N'-2,4,6-trimethylphenylsulfonyl-guanidino)-1(S)-[4-(N'-2,4,6-trimethylphenylsulfonyl-guanidino)-1(S)-(1-naphthalen-1(S)-yl-ethylcarbamoyl)-butylcarbamoyl]-butyl}-carbamic acid tert-butyl ester 
• 905593-26-2 Boc-Arg(Mts)-Arg(Mts)-NMe(OMe) 
• 905593-24-0 [4-(N'-2,4,6-trimethylphenylsulfonyl-guanidino)-1(S)-(1-naphthalen-1(S)-yl-ethylcarbamoyl)-butyl]-carbamic acid tert-butyl ester 
• 452068-20-1 α-conotoxin peptide 
• 134303-68-7 Boc-Arg(Mts)-cyclooctylamine 
• 120614-99-5 Boc-Arg(Mts)-hexamethyleneimine 

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.