38155-18-9Relevant academic research and scientific papers
Utilization of 2-(4-Nitrophenylsulfonyl)ethoxycarbonyl (Nsc) as a substitute for 9H-fluoren-9-ylmethoxycarbonyl (Fmoc) in liquid phase chemistry
Maier, Thomas C.,Podlech, Joachim
, p. 727 - 730 (2004)
2-(4-Nitrophenylsulfonyl)ethoxycarbonyl (Nsc) is a useful substitute for the Fmoc group. It is easily removed not only with secondary amines but with tris(aminoethyl)amine (TAEA) and with resin-bound TAEA, thus allowing for a simplified work-up: the side products of the deprotection are removed either by extraction with phosphate buffer or by filtration.
Liquid Phase Peptide Synthesis via One-Pot Nanostar Sieving (PEPSTAR)
Yeo, Jet,Peeva, Ludmila,Chung, Seoyeon,Gaffney, Piers,Kim, Daeok,Luciani, Carla,Tsukanov, Sergey,Seibert, Kevin,Kopach, Michael,Albericio, Fernando,Livingston, Andrew
supporting information, p. 7786 - 7795 (2021/03/01)
Herein, a one-pot liquid phase peptide synthesis featuring iterative addition of amino acids to a “nanostar” support, with organic solvent nanofiltration (OSN) for isolation of the growing peptide after each synthesis cycle is reported. A cycle consists of coupling, Fmoc removal, then sieving out of the reaction by-products via nanofiltration in a reactor-separator, or synthesizer apparatus where no phase or material transfers are required between cycles. The three-armed and monodisperse nanostar facilitates both efficient nanofiltration and real-time reaction monitoring of each process cycle. This enabled the synthesis of peptides more efficiently while retaining the full benefits of liquid phase synthesis. PEPSTAR was validated initially with the synthesis of enkephalin-like model penta- and decapeptides, then octreotate amide and finally octreotate. The crude purities compared favorably to vendor produced samples from solid phase synthesis.
A dipeptide-based superhydrogel: Removal of toxic dyes and heavy metal ions from waste water
Nandi, Nibedita,Baral, Abhishek,Basu, Kingshuk,Roy, Subhasish,Banerjee, Arindam
, (2017/02/05)
A short peptide-based molecule has been found to form a strong hydrogel at phosphate buffer solution of pH 7.46. The hydrogel has been characterized thoroughly using various techniques including field emission scanning electron microscopy (FE-SEM), wide angle powder X-ray diffraction (PXRD), and rheological analysis. It has been observed from FE-SEM images that entangled nanofiber network is responsible for gelation. Rheological investigation demonstrates that the self-assembly of this synthetic dipeptide results in the formation of mechanically strong hydrogel with storage modulus (G′) around 104 Pa. This gel has been used for removing both cationic and anionic toxic organic dyes (Brilliant Blue, Congo red, Malachite Green, Rhodamine B) and metal ions (Co2+ and Ni2+) from waste water. Moreover, only a small amount of the gelator is required (less than 1 mg/mL) for preparation of this superhydrogel and even this hydrogel can be reused three times for dye/metal ion absorption. This signifies the importance of the hydrogel towards waste water management.
Towards the first total synthesis and anticancer screening of polycarponin C: A cyclic octapeptide
Shinde, Nirmala V.,Dhake, Avinash S.,Havalavalaval, Kishan P.
, p. 515 - 521 (2016/05/09)
The present study describes designing, synthesis and anticancer screening of a proline rich cyclic octapeptide polycarponin C, by solution phase synthesis. The synthesis was carried out by coupling a tetrapeptide Boc-Pro-Thr-Leu-Pro-OH with another tetrap
Room temperature N-arylation of amino acids and peptides using copper(i) and β-diketone
Sharma, Krishna K.,Sharma, Swagat,Kudwal, Anurag,Jain, Rahul
supporting information, p. 4637 - 4641 (2015/04/27)
A mild and efficient method for the N-arylation of zwitterionic amino acids, amino acid esters and peptides is described. The procedure provides the first room temperature synthesis of N-arylated amino acids and peptides using CuI as a catalyst, diketone as a ligand, and aryl iodides as coupling partners. The method is equally applicable for using relatively inexpensive aryl bromides as coupling partners at 80 °C. Using this procedure, electronically and sterically diverse aryl halides, containing reactive functional groups were efficiently coupled in good to excellent yields.
PEPTIDE EPOXYKETONE COMPOUNDS
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Paragraph 00267; 00269, (2014/02/16)
The present disclosure relates to novel compounds and pharmaceutical compositions thereof which are useful as inhibitors of proteasomes. The compounds provided herein are capable of inhibiting all three of CT-L, T-L, and PGPH activities of proteasomes, and are useful in treating various conditions or diseases associated with proteasomes.
Synthesis of sansalvamide A peptidomimetics: Triazole, oxazole, thiazole, and pseudoproline containing compounds
Davis, Melinda R.,Singh, Erinprit K.,Wahyudi, Hendra,Alexander, Leslie D.,Kunicki, Joseph B.,Nazarova, Lidia A.,Fairweather, Kelly A.,Giltrap, Andrew M.,Jolliffe, Katrina A.,McAlpine, Shelli R.
experimental part, p. 1029 - 1051 (2012/02/15)
Peptidomimetic-based macrocycles typically have improved pharmacokinetic properties over those observed with peptide analogs. Described are the syntheses of 13 peptidomimetic derivatives that are based on active sansalvamide A structures, where these analogs incorporate heterocycles (triazoles, oxazoles, thiazoles, or pseudoprolines) along the macrocyclic backbone. The syntheses of these derivatives employ several approaches that can be applied to convert a macrocyclic peptide into its peptidomimetic counterpart. These approaches include peptide modifications to generate the alkyne and azide for click chemistry, a serine conversion into an oxazole, a Hantzsch reaction to generate the thiazole, and protected threonine to generate the pseudoproline derivatives. Furthermore, we show that two different peptidomimetic moieties, triazoles, and thiazoles, can be incorporated into the macrocyclic backbone without reducing cytotoxicity: triazole and thiazole.
Design and synthesis of Hsp90 inhibitors: Exploring the SAR of Sansalvamide A derivatives
Sellers, Robert P.,Alexander, Leslie D.,Johnson, Victoria A.,Lin, Chun-Chieh,Savage, Jeremiah,Corral, Ricardo,Moss, Jason,Slugocki, Tim S.,Singh, Erinprit K.,Davis, Melinda R.,Ravula, Suchitra,Spicer, Jamie E.,Oelrich, Jenna L.,Thornquist, Andrea,Pan, Chung-Mao,McAlpine, Shelli R.
experimental part, p. 6822 - 6856 (2010/10/18)
Utilizing the structure-activity relationship we have developed during the synthesis of the first two generations and mechanism of action studies that point to the interaction of these molecules with the key oncogenic protein Hsp90, we report here the design of 32 new Sansalvamide A derivatives and their synthesis. Our new structures, designed from previously reported potent compounds, were tested for cytotoxicity on the HCT116 colon cancer cell line, and their binding to the biological target was analyzed using computational studies involving blind docking of derivatives using Autodock. Further, we show new evidence that our molecules bind directly to Hsp90 and modulate Hsp90's binding with client proteins. Finally, we demonstrate that we have integrated good ADME properties into a new derivative.
Stereo-controlled synthesis of novel photoreactive γ-secretase inhibitors
Yang, Guangli,Yin, Ye Ingrid,Chun, Jiong,Shelton, Christopher C.,Ouerfelli, Ouathek,Li, Yue-Ming
scheme or table, p. 922 - 925 (2009/10/15)
The stereoselective synthesis of novel photoreactive γ-secretase inhibitors 2 and 3 has been achieved. Key steps of the strategy involve preparation of α-N-Boc-epoxide 8 and formation of lactone 14 in a practical and stereo-controlled fashion. Compounds 2
Comprehensive study of sansalvamide A derivatives and their structure-activity relationships against drug-resistant colon cancer cell lines
Otrubova, Katerina,Lushington, Gerald,Vander Velde, David,McGuire, Kathleen L.,McAlpine, Shelli R.
, p. 530 - 544 (2008/09/18)
We report an extensive structure-activity relationship (SAR) of 62 compounds active against two drug-resistant colon cancer cell lines. Our comprehensive evaluation of two generations of compounds utilizes SAR, NMR, and molecular modeling to evaluate the
