74939-28-9Relevant 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
Design, synthesis and evaluation of inhibitor of apoptosis protein (IAP) antagonists that are highly selective for the BIR2 domain of XIAP
Ardecky, Robert J.,Welsh, Kate,Finlay, Darren,Lee, Pooi San,González-López, Marcos,Ganji, Santhi Reddy,Ravanan, Palaniyandi,Mace, Peter D.,Riedl, Stefan J.,Vuori, Kristiina,Reed, John C.,Cosford, Nicholas D.P.
, p. 4253 - 4257 (2013/07/26)
We recently reported the systematic ligand-based rational design and synthesis of monovalent Smac mimetics that bind preferentially to the BIR2 domain of the anti-apoptotic protein XIAP. Expanded structure-activity relationship (SAR) studies around these peptidomimetics led to compounds with significantly improved selectivity (>60-fold) for the BIR2 domain versus the BIR3 domain of XIAP. The potent and highly selective IAP antagonist 8q (ML183) sensitized TRAIL-resistant prostate cancer cells to apoptotic cell death, highlighting the merit of this probe compound as a valuable tool to investigate the biology of XIAP.
Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents
Suhas, Ramesh,Channe Gowda, Dase
experimental part, p. 850 - 862 (2012/06/04)
A series of new aurantiamide acetate analogues were synthesized by modifying its N-terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti-inflammatory activity against carrageenan-induced oedema in albino rats at different doses (25, 50 and 100mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.
Design and synthesis of tryptophan containing peptides as potential analgesic and anti-inflammatory agents
Suhas,Gowda, D.Channe
scheme or table, p. 535 - 540 (2012/09/22)
A new series of smaller peptides with tryptophan at C-terminal and varying N-protected amino acids/peptides were designed, synthesized and characterized by analytical and spectroscopic techniques. Analgesic and anti-inflammatory properties of these peptides were carried out in vivo using tail-flick method and carrageenan-induced paw edema method, respectively, at different doses and different time intervals. Most of the peptides synthesized displayed enhanced activity, and particularly tetra and hexapeptides 29-31 were found to be even more potent than the reference standards used. Moreover, some peptides have exhibited promising activity even after 24h of administration, whereas the reference standards were active only up to 3h. Further, the compounds did not present any ulcerogenic liability.
Development of supramolecular organo-gel based on tripeptide skeletons
Azuma, Eriko,Kuramochi, Kouji,Tsubaki, Kazunori
body text, p. 680 - 684 (2010/07/15)
Boc-Ser-Val-Gly-OCH2Ph (31) showed high gelation abilities in the aromatic solvents, particularly in toluene. The minimum gelation concentration of 31 in toluene was 10 mg/ml, suggesting that 2500 molecules of toluene were immobilized by each m
HOBt·DCHA-mediated synthesis of sterically hindered peptides employing Fmoc-amino acid chlorides in both solution-phase and solid phase methods
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Chenna Krishna
, p. 2625 - 2637 (2008/12/22)
The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF-CH2Cl2 has also been outlined. The final peptide was obtained in 80% yield and was fully characterized. Copyright Taylor & Francis Group, LLC.
Rapid and efficient synthesis of peptide fragments containing α- aminoisobutyric acid using Fmoc-amino acid chlorides/potassium salt of 1- hydroxybenzotriazole
Suresh Babu, Vommina V.,Gopi, Hosahudya N.
, p. 1049 - 1050 (2007/10/03)
The synthesis of peptides containing multiple Aib residues was accomplished using Fmoc-Aib-Cl in presence of KOBt. As no additional base was added, the duration of coupling reactions could be extended. Thus, the synthesis of the alamethicin 1-4 fragment, Aib-Pro-Aib-Ala, the emerimicin 2- 6 fragment, Aib-Aib-Aib-Val-Gly and the Aib tetramer, Fmoc-(Aib)4-OBzl were accomplished in good yield and purity.
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).
