128557-46-0Relevant academic research and scientific papers
Bispidine as a helix inducing scaffold: Examples of helically folded linear peptides
Haridas,Sadanandan, Sandhya,Gopalakrishna,Bijesh,Verma, Ram. P.,Chinthalapalli, Srinivas,Shandilya, Ashutosh
, p. 10980 - 10982 (2013)
We designed and synthesized bispidine-anchored peptides and showed that these peptides as small as B3 (containing four chiral α-amino acid residues) adopt a right handed helical conformation. Bispidine anchored linear peptide B3 adopts a helical conformat
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.
Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs
Zhang, Jiyun,Wen, Hongmei,Shen, Fei,Wang, Xinzhi,Shan, Chenxiao,Chai, Chuan,Liu, Jian,Li, Wei
, (2019/08/26)
Curcumin (CUR) is a natural yellow pigment from turmeric with extensive bioactivities. However its relatively poor solubility limited its absorption and bioavailability. In this study, a novel series of CUR-peptide conjugates were designed and synthesized
Antioxidant activity of peptide-based angiotensin converting enzyme inhibitors
Bhuyan, Bhaskar J.,Mugesh, Govindasamy
, p. 2237 - 2247 (2012/04/10)
Angiotensin converting enzyme (ACE) inhibitors are important for the treatment of hypertension as they can decrease the formation of vasopressor hormone angiotensin II (Ang II) and elevate the levels of vasodilating hormone bradykinin. It is observed that bradykinin contains a Ser-Pro-Phe motif near the site of hydrolysis. The selenium analogues of captopril represent a novel class of ACE inhibitors as they also exhibit significant antioxidant activity. In this study, several di- and tripeptides containing selenocysteine and cysteine residues at the N-terminal were synthesized. Hydrolysis of angiotensin I (Ang I) to Ang II by ACE was studied in the presence of these peptides. It is observed that the introduction of l-Phe to Sec-Pro and Cys-Pro peptides significantly increases the ACE inhibitory activity. On the other hand, the introduction of l-Val or l-Ala decreases the inhibitory potency of the parent compounds. The presence of an l-Pro moiety in captopril analogues appears to be important for ACE inhibition as the replacement of l-Pro by l-piperidine 2-carboxylic acid decreases the ACE inhibition. The synthetic peptides were also tested for their ability to scavenge peroxynitrite (PN) and to exhibit glutathione peroxidase (GPx)-like activity. All the selenium-containing peptides exhibited good PN-scavenging and GPx activities. The Royal Society of Chemistry 2012.
A novel L-amino acid ligase from bacillus subtilis NBRC3134 catalyzed oligopeptide synthesis
Kino, Kuniki,Arai, Toshinobu,Tateiwa, Daisuke
experimental part, p. 129 - 134 (2010/04/24)
L-Amino acid ligase catalyzes dipeptide synthesis from unprotected L-amino acids in an ATP-dependent manner. We have purified a new L-amino acid ligase, RizA, which synthesizes dipeptides whose N-terminus is Arg, from Bacillus subtilis NBRC3134, a microorganism that produces a rhizocticin peptide antibiotic. It was suggested that RizA is probably involved in rhizocticin biosynthesis. In this study, we performed sequence analysis of unknown regions around rizA, and newly identified a gene that encodes a protein that possesses an ATP-grasp motif upstream of rizA. This gene was designated rizB, and its recombinant protein was prepared. Recombinant RizB synthesized homo-oligo-mers of branched-chain L-amino acids and L-methionine consisting of two to five amino acids in an ATP-dependent manner. RizB also synthesized various heteropeptides. Further examination showed that RizB might elongate a peptide chain at the N-terminus. This is the first report on an L-amino acid ligase catalyzing oligopeptide synthesis.
Synthesis of second-generation Sansalvamide A derivatives: Novel templates as potential antitumor agents
Rodriguez, Rodrigo A.,Pan, Po-Shen,Pan, Chung-Mao,Ravula, Suchitra,Lapera, Stephanie,Singh, Erinprit K.,Styers, Thomas J.,Brown, Joseph D.,Cajica, Julia,Parry, Emily,Otrubova, Katerina,McAlpine, Shelli R.
, p. 1980 - 2002 (2007/10/03)
We report the synthesis of 34 second-generation Sansalvamide A derivatives. San A derivatives have unique anticancer properties and target multiple cancers, including colon, pancreatic, breast, prostate, and melanoma. As novel templates, the derivatives d
Synthesis of Sansalvamide A derivatives and their cytotoxicity in the MSS colon cancer cell line HT-29
Styers, Thomas J.,Kekec, Ahmet,Rodriguez, Rodrigo,Brown, Joseph D.,Cajica, Julia,Pan, Po-Shen,Parry, Emily,Carroll, Chris L.,Medina, Irene,Corral, Ricardo,Lapera, Stephanie,Otrubova, Katerina,Pan, Chung-Mao,McGuire, Kathleen L.,McAlpine, Shelli R.
, p. 5625 - 5631 (2007/10/03)
We report the synthesis of thirty-six Sansalvamide A derivatives, and their biological activity against colon cancer HT-29 cell line, a microsatellite stable (MSS) colon cancer cell-line. The thirty-six compounds can be divided into three subsets, where t
Structures, sensory activity, and dose/response functions of 2,5-diketopiperazines in roasted cocoa nibs (Theobroma cacao)
Stark, Timo,Hofmann, Thomas
, p. 7222 - 7231 (2007/10/03)
The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and i
β-sheet ligands in action: KLVFF recognition by aminopyrazole hybrid receptors in water
Rzepecki, Petra,Schrader, Thomas
, p. 3016 - 3025 (2007/10/03)
Little is known about the precise mechanism of action of β-sheet ligands, hampered by the notorious solubility problems involved with protein misfolding and amyloid formation. Recently the nucleation site for the pathogenic aggregation of the Alzheimer's
Application of nim-2,6-dimethoxybenzoyl histidine in solid-phase peptide synthesis
Zaramella, Simone,Stroemberg, Roger,Yeheskiely, Esther
, p. 2454 - 2461 (2007/10/03)
Fmoc-histidine derivatives protected with 2,6-dimethoxybenzoyl (2,6-Dmbz) units, either on the τ- (1) or on the π-position (2) of the imidazole residue, have been prepared and applied to the synthesis of the dipeptide Fmoc-His(2,6-Dmbz)-Val-OMe, with high coupling efficiencies (99 and 95%, respectively) and low racemization (0.3 and 0.1%, respectively), as ascertained by HPLC analysis on the fully protected dipeptides. In addition, the hexapeptide H-Ala-Ser-Val-His-Val-Phe-OH (I) has been synthesized on a solid support employing the novel building blocks 1 and 2 as well as commercially available Fmoc-His(t-Trt)-OH (3). The crude deprotected products were analyzed by reverse-phase HPLC and mass spectrometry, which indicated that when the τ-protected derivatives 1 and 3 were employed the products were of comparable quality (93-94% major peak). The hexapeptide synthesized with the π-protected histidine 2 was contaminated with a product corresponding to 2,6-Dmbz-His-Val-Phe-OH (12), which was probably formed through the intramolecular acyl transfer of a 2,6-Dmbz unit from the π-nitrogen atom to the α-amino group of the N-terminal histidine unit upon removal of the Fmoc group. This side reaction was insignificant (less than 0.5%) when using the τ-protected derivative 1. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
