922500-95-6Relevant academic research and scientific papers
Macrocyclisation of small peptides enabled by oxetane incorporation
Roesner, Stefan,Saunders, George J.,Wilkening, Ina,Jayawant, Eleanor,Geden, Joanna V.,Kerby, Paul,Dixon, Ann M.,Notman, Rebecca,Shipman, Michael
, p. 2465 - 2472 (2019)
Cyclic peptides are an important source of new drugs but are challenging to produce synthetically. We show that head-to-tail peptide macrocyclisations are greatly improved, as measured by isolated yields, reaction rates and product distribution, by substi
BROAD SPECTRUM ANTI-CANCER COMPOUNDS
-
Page/Page column 285, (2021/04/23)
Described herein, inter alia, are compounds for treating cancer and methods of use. This disclosure features chemical entities (e.g., small hairpin RNAs (shRNAs), micro RNA (miRNAs), small interfering RNA (siRNAs), small molecule inhibitors, antisense nucleic acids, peptides, viruses, CRISPR-sgRNAs, or combinations thereof) that inhibit one or more of m6A writers (e.g., methyltransferase like 3 (Mettl3 or MT-A70) or methyltransferase like-14 (Mettl14)), m6Am writers (e.g., phosphorylated CTD interacting factor I (PCIF 1), or Mettl3/14), m6A erasers (e.g., fat-mass and obesity-associated protein (FTO) or ALKB homolog 5 (ALKBH5)), m6Am erasers (e.g., FTO), m6A readers (e.g., YTH domain-containing family proteins (YTHs)), YTF domain family member 1 (YTHDF 1), YTF domain family member 2 (YTHDF 2), YTF domain family member 3 (YTHDF 3), or tyrosine-protein phosphatase non-receptor type 2 (PTPN2).
Development of oxetane modified building blocks for peptide synthesis
Beadle, Jonathan D.,Clarkson, Guy J.,Raubo, Piotr,Roesner, Stefan,Shipman, Michael,Tam, Leo K. B.,Wilkening, Ina
supporting information, p. 5400 - 5405 (2020/08/03)
The synthesis and use of oxetane modified dipeptide building blocks in solution and solid-phase peptide synthesis (SPPS) is reported. The preparation of building blocks containing non-glycine residues at the N-terminus in a stereochemically controlled man
Enzymatically-stable oxetane-based dipeptide hydrogels
McDougall, Laura,Draper, Emily R.,Beadle, Jonathan D.,Shipman, Michael,Raubo, Piotr,Jamieson, Andrew G.,Adams, Dave J.
supporting information, p. 1793 - 1796 (2018/02/21)
Low molecular weight gelators that are not easily degraded by enzymes have a range of potential applications. Here, we report new Fmoc-protected dipeptides in which the amide carbonyl group has been replaced by an oxetane ring. Remarkably one of these peptidomimetics, but not the corresponding dipeptide, is an effective gelator, forming hydrogels at a concentration of 3 mg mL-1. On assembly, there is a lack of beta-sheet structure, implying that there is no requirement for this motif in such a gel. Furthermore, the modified dipeptide is also stable to proteolysis compared to the parent dipeptide.
Method for taking DAST reagent as removing reagent to synthetize conjugated nitroolefin substituted series derivative
-
Paragraph 0060; 0061; 0064; 0065, (2018/12/13)
The invention discloses a preparation method of taking a DAST reagent as a removing reagent to synthesize a conjugated nitroolefin substituted series derivative. The preparation method comprises the following steps that a carbonyl compound (compound II) i
Synthesis of 6-Azaspiro[4.3]alkanes: Innovative Scaffolds for Drug Discovery
Chalyk, Bohdan A.,Isakov, Andrei A.,Butko, Maryna V.,Hrebeniuk, Kateryna V.,Savych, Olena V.,Kucher, Olexandr V.,Gavrilenko, Konstantin S.,Druzhenko, Tetiana V.,Yarmolchuk, Vladimir S.,Zozulya, Sergey,Mykhailiuk, Pavel K.
, p. 4530 - 4542 (2017/08/30)
New scaffolds for drug discovery, 6-azaspiro[4.3]alkanes, have been synthesized in two steps from four-membered-ring ketones: cyclobutanone, thienone, N-Boc-azetidinone (Boc = tert-butoxycarbonyl), etc. The key transformation was the reaction between electron-deficient exocyclic alkenes and an in-situ generated N-benzylazomethine ylide.
Solid-Phase Synthesis of Oxetane Modified Peptides
Beadle, Jonathan D.,Knuhtsen, Astrid,Hoose, Alex,Raubo, Piotr,Jamieson, Andrew G.,Shipman, Michael
supporting information, p. 3303 - 3306 (2017/06/23)
Solid-phase peptide synthesis (SPPS) is used to create peptidomimetics in which one of the backbone amide C=O bonds is replaced by a four-membered oxetane ring. The oxetane containing dipeptide building blocks are made in three steps in solution, then integrated into peptide chains by conventional Fmoc SPPS. This methodology is used to make a range of peptides in high purity including backbone modified derivatives of the nonapeptide bradykinin and Met- and Leu-enkephalin.
Synthesis of Oxetane- and Azetidine-Containing Spirocycles Related to the 2,5-Diketopiperazine Framework
Beadle, Jonathan D.,Powell, Nicola H.,Raubo, Piotr,Clarkson, Guy J.,Shipman, Michael
supporting information, p. 169 - 172 (2015/12/26)
A simple two-step sequence is used to efficiently make novel spirocyclic analogues of the diketopiperazine nucleus. Conjugate addition of chiral α-amino esters to nitroalkenes, generated from oxetan-3-one or N-Boc-azetidin-3-one, followed by nitro group r
HEPATITIS B CORE PROTEIN ALLOSTERIC MODULATORS
-
Paragraph 000279, (2015/10/05)
ABSTRACT The present disclosure provides, in part, compounds having allosteric effector properties against Hepatitis B virus Cp. Also provided herein are methods of treating viral infections, such as hepatitis B, comprising administering to a patient in need thereof a disclosed compound.
Synthesis and structure of oxetane containing tripeptide motifs
Powell, Nicola H.,Clarkson, Guy J.,Notman, Rebecca,Raubo, Piotr,Martin, Nathaniel G.,Shipman, Michael
supporting information, p. 8797 - 8800 (2014/07/22)
A new class of peptidomimetic is reported in which one of the amide CO bonds of the peptide backbone is replaced by an oxetane ring. They are synthesised by conjugate addition of various α-amino esters to a 3-(nitromethylene)oxetane, reduction of the nitro group and further coupling with N-Z protected amino acids to grow the peptide chain. Structural insights are provided by X-ray diffraction and molecular dynamics simulations.
