112160-37-9

Usage

Chemical Properties

White powder

InChI:InChI=1/C20H32N4O5S/c1-11-12(2)17(13(3)14-8-9-20(4,5)29-16(11)14)30(27,28)24-19(22)23-10-6-7-15(21)18(25)26/h15H,6-10,21H2,1-5H3,(H,25,26)(H3,22,23,24)/t15-/m0/s1

Upstream product

• 112160-39-1 2,2,5,7,8-pentamethylchroman-6-sulfonyl chloride 
• 112160-32-4 C₂₈H₃₈N₄O₇S 
• 200125-12-8 N²-(tert-butoxycarbonyl)-N^ω-((2,2,5,7,8-pentamethylchroman-6-yl)sulfonyl)-L-arginine 
• 112160-32-4 N_α-benzyloxycarbonyl-N_G-(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-L-arginine 
• 78-79-5 isoprene 
• 697-82-5 2,3,5-trimethylphenol 
• 55646-01-0 2,2,5,7,8-pentamethyl-chromane 

Downstream Products

• 119831-72-0 Fmoc-Arg(Pbf)-OH 
• 1182714-00-6 RGVGFIRF 
• 1239956-91-2 (S)-2-(3-(3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorophenyl)ureido)-5-guanidinopentanoic acid 
• 503173-71-5 L-aspartic acid, N-[(phenylmethoxy)carbonyl]glycyl-N⁵-({[(3,4-dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-yl)sulfonyl]amino}iminomethyl)-L-ornithylglycyl,-bis(1,1-dimethylethyl) ester 
• 221665-14-1 N-α-[N-(benzyloxycarbonyl)aminocaproyl]-N-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)arginine methyl ester 
• 221665-13-0 N-α-[N-(benzyloxycarbonyl)-β-alanyl]-N-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)arginine methyl ester 
• 221665-12-9 N-α-[N-(benzyloxycarbonyl)aminocaproyl]-N-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)arginine 
• 221665-11-8 N-α-[N-(benzyloxycarbonyl)-β-alanyl]-N-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)arginine 

Relevant academic research and scientific papers

APPLICATION OF THE NG-(2,2,5,7,8-PENTAMETHYLCHROMAN-6-SULPHONYL) DERIVATIVE OF FMOC-ARGININE TO PEPTIDE SYNTHESIS

The trifluoroacetic acid labile pentamethylchromanylsulphonyl protecting group for the guanidino group of arginine has been used in conjunction with the base-labile Fmoc Nα protecting group for the synthesis of arginine-containing peptides.

Chemoselective deprotection of N-Boc group in amino acids and peptides by bismuth(III) trichloride

Selective deprotection of N-Boc group was achieved in excellent yields using bismuth(III) trichloride in a mixed solvent of acetonitrile and water (50:1, v/v) at 55°C. Acid-labile groups such as Pmc and tert-butyl ester were not affected and no alkylation of tryptophan, methionine, and cysteine residues was observed under the deprotection conditions.

An acid labile arginine derivative for peptide synthesis: N(G)-2,2,5,7,8-pentamethylchroman-6-sulphonyl-L-arginine

A trifluoroacetic acid (TFA) labile protecting group for the guanidine side chain function of arginine has been developed. N(G)-(2,2,5,7,8-Pentamethylchroman-6-sulphonyl-L-arginine is cleaved rapidly in TFA or 50% TFA in dichloromethane at room temperatur

Peptide Synthesis by Prior Thiol Capture. 6. Rates of the Disulfide Bond Forming Capture Reaction and Demonstration of the Overall Strategy by Synthesis of the C-Terminal 29-Peptide Sequence of BPTI

Peptide bond formation by prior thiol capture involves as a first step formation of a disulfide bond between two S-functionalized peptide fragments, one bearing a 4-(acyloxy)-6-mercaptodibenzofuran at its C-terminus, the other bearing an S-activated cysteine residue at its N-terminus.The Scm procedure (Scm MeO-CO-S) of Brois and others is used to generate disulfides of general structure -Cys(S-S-Ar)- by reaction of suitable arene thiols with -Cys(S-Scm)- derivatives.Mixtures of hexafluoroisopropyl alcohol (HFIP) with water and acetonitrile facilitate this reaction, which is markedly accelerated by traces of tertiary amines, by electron-withdrawing groups near the Scm function, and by an increase in the fraction of water in the mixture.A 94percent yield in 5 min was seen for reaction of the trifluoroacetate salt of H-L-Cys(S-Scm)-OMe (5*10-4 M) with 4-mercaptodibenzofuran (5*10-4 M) in 9:1 HFIP-MeCN.The scope of the thiol capture strategy is demonstrated by a four-fragment, three-stage assembly of the 29-peptyde sequence 30-58 of the protein basic pancreatic trypsin inhibitor (BPTI).

NG-2,2,5,7,8-PENTAMETHYLCHROMAN-6-SULPHONYL-L-ARGININE: A NEW ACID LABILE DERIVATIVE FOR PEPTIDE SYNTHESIS

A new acid labile protecting group for the guanido side chain functionality of arginine has been developed.NG-(2,2,5,7,8-Pentamethylchroman-6-sulphonyl)-L-arginine, prepared from Nα-benzyloxycarbonyl-L-arginine and 2,2,5,7,8-pentamethylchroman-6-sulphonyl chloride, is cleaved rapidly in trifluoroacetic acid (TFA) or 50percent TFA in dichloromethane at room temperature.