47094-27-9Relevant academic research and scientific papers
Functionalization of Sulfonamide-Containing Peptides through Late-Stage Palladium-Catalyzed C(sp3)-H Arylation
Bai, Qingqing,Tang, Jian,Wang, Huan
supporting information, p. 5858 - 5861 (2019/08/27)
Bioactive peptides are emerging as promising candidates of clinic therapeutics. Here, we report a method for late-stage functionalization of sulfonamide-containing peptides through Pd-catalyzed C(sp3)-H arylation. In this protocol, the backbone
Hydrophobicity profile of amino acid residues: A differential scanning calorimetry and circular dichroism study of leucine and isoleucine co-polypeptides of the protein-based polymers of elastin
Gowda, D. Channe,Baba, A. Ramesha,Luan, Chi-Hao
, p. 2606 - 2613 (2007/10/03)
The inverse temperature transition of hydrophobic folding and assembly of a "host-guest" model system based on the elastin derived polypentapeptide, poly(VPGVG), is employed to determine the relative hydrophobicity of amino acid residues of proteins and p
Synthesis and biological activity of the prodrug of class I major histocompatibility peptide GILGFVFTL activated by β-glucuronidase
Rawale, Sharad,Hrihorczuk, Lew M.,Wei, Wei-Zen,Zemlicka, Jiri
, p. 937 - 943 (2007/10/03)
The first synthesis of a prodrug of HLA-A2.1 associated antigenic influenza peptide 2a was accomplished. Two methods for synthesis of prodrugs of antigenic peptides activated by β-glucuronidase and comprising a self-immolative 3-nitrobenzyloxycarbonyl moiety were investigated. Reaction of β-glucuronic acid glycoside of 4-hydroxy-3-nitrobenzyl alcohol (3) with N,N′-disuccinimidyl carbonate (DSC) followed by conjugation with AlaOMe, Gly, Thr, Phe-Leu, and Leu-Arg gave carbamates 4a-4f. Deacetylation of 4b and 4e with MeONa/MeOH gave β-glucuronides 5b and 5e. Compound 5e was converted to β-glucuronic acid conjugate 6e by the action of pig liver esterase (PLE). Compound 6e is a substrate for β-glucuronidase. Method of a direct introduction of the prodrug residue into antigenic nonapeptide GILGFVFTL (2b) failed. Alternately, glycine conjugate 5b was activated to pentafluorophenyl ester 10. Model coupling of 10 with Phe-Leu gave tripeptide conjugate ester 11a which was hydrolyzed by PLE to uronic acid 12. Condensation of 10 with octapeptide ILGFVFTL (9) gave prodrug precursor 11b. Octapeptide 9 was prepared by de novo synthesis using a racemization-free fragment coupling method. Ester hydrolysis with Ba(OH)2/MeOH gave the target prodrug 2a which is a substrate for β-glucuronidase. Prodrug 2a does not bind to HLA-A2.1 of T2 human cells defective in major histocompatibility complex I (MHC I)-associated peptide processing. Addition of β-glucuronidase restored the binding to the level observed with parent nonapeptide 2b although higher concentrations of prodrug 2a and enzyme were necessary.
ANTIHERPETIC AGENTS
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, (2008/06/13)
A series of carboxyl-containing N-alkyldipeptides have been found to posess antiviral potency-specifically against herpes simplex virus-by selectively inhibiting the viral ribonucleotide reductase enzyme
ATRIOPEPTINS. I. SYNTHESIS OF C-TERMINAL FRAGMENTS
Ovchinnikov, Mikhail V.,Bespalova, Zhanna D.,Molokoedov, Aleksandr S.,Revenko, Inna V.,Sepetov, Nikolai F.,et al
, p. 772 - 783 (2007/10/02)
Peptides, corresponding to the C-terminal sequence in atriopeptins, have been synthesized using classical methods of peptide synthesis in solution and characterized by various physicochemical methods.The synthetic strategy and methods are discussed.
The Steric Hindrance of the Stepwise Reaction of N-Carboxy α-Amino Acid Anhydride with the α-Amino Acid Ester
Oya, Masanao,Takahashi, Tomoko
, p. 2705 - 2707 (2007/10/02)
The mechanisms of the reactions of 4-alkyloxazolidinediones (1) (N-carboxy α-amino acid anhydrides(NCAs)) with α-amino acid benzyl ester p-toluenesulfonates (2) were investigated in acetonitrile containing triethylamine at low and room temperatures.Two types of reactions were observed: (1) the polymerization of NCAs was initiated with a small amount of 2 to produce polypeptides (6), and (2) the dipeptide benzyl esters (4) were produced by the stepwise reaction of NCAs with the esters.Both the polymerization and the dipeptide formation (1+2) seemed to be initiated by the nucleophilic attack of the amino group of the ester on the C-5 carbon of NCAs.The polymerization proceeded when the side chains of the amino acid esters (R2) were more bulky than those of the NCAs (R1).On the contrary, dipeptide esters were produced when the side chains of the NCAs (R1) were more bulky than those of the esters (R2).
