187526-99-4Relevant academic research and scientific papers
Urea based foldamers
Yoo, Sung Hyun,Li, Bo,Dolain, Christel,Pasco, Morgane,Guichard, Gilles
, p. 59 - 92 (2021/06/25)
N,N′-linked oligoureas are a class of enantiopure, sequence-defined peptidomimetic oligomers without amino acids that form well-defined and predictable helical structures akin to the peptide α-helix. Oligourea-based foldamers combine a number of features—such as synthetic accessibility, sequence modularity, and folding fidelity—that bode well for their use in a range of applications from medicinal chemistry to catalysis. Moreover, it was recently recognized that this synthetic helical backbone can be combined with regular peptides to generate helically folded peptide-oligourea hybrids that display additional features in terms of helix mimicry and protein-surface recognition properties. Here we provide detailed protocols for the preparation of requested monomers and for the synthesis and purification of homo-oligoureas and peptide-oligourea hybrids.
Sequencing of Sequence-Defined Oligourethanes via Controlled Self-Immolation
Anslyn, Eric V.,Coronado, Jaime N.,Dahlhauser, Samuel D.,Escamilla, P. Rogelio,Glass, Samuel A.,Moor, Sarah R.,Rapagnani, Rachel M.,Saunders, Douglas P.,Shei, Jasper S.,Vandewalle, Abigail N.,York, Jordan T.
supporting information, p. 2744 - 2749 (2020/03/10)
Sequence-defined polymers show promise for biomimetics, self-assembly, catalysis, and information storage, wherein the primary structure begets complex chemical processes. Here we report the solution-phase and the high-yielding solid-phase syntheses of discrete oligourethanes and methods for their self-immolative sequencing, resulting in rapid and robust characterization of this class of oligomers and polymers, without the use of MS/MS. Crucial to the sequencing is the inherent reactivity of the terminal alcohol to "unzip" the oligomers, in a controlled and iterative fashion, releasing each monomer as a 2-oxazolidinone. By monitoring the self-immolation reaction via LC/MS, an applied algorithm rapidly produces the sequence of the oligourethane. Not only does this process provide characterization of structurally complex molecules, it works as a reader of molecular information.
Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates
Santhosh,Durgamma,Shekharappa,Sureshbabu, Vommina V.
, p. 4874 - 4880 (2018/07/15)
A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.
Fast and Facile Synthesis of 4-Nitrophenyl 2-Azidoethylcarbamate Derivatives from N-Fmoc-Protected α-Amino Acids as Activated Building Blocks for Urea Moiety-Containing Compound Library
Chen, Ying-Ying,Chang, Li-Te,Chen, Hung-Wei,Yang, Chia-Ying,Hsin, Ling-Wei
, p. 131 - 136 (2017/04/24)
A fast and facile synthesis of a series of 4-nitrophenyl 2-azidoethylcarbamate derivatives as activated urea building blocks was developed. The N-Fmoc-protected 2-aminoethyl mesylates derived from various commercially available N-Fmoc-protected α-amino ac
Tin(ii) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement
Bandyopadhyay, Anupam,Agrawal, Neha,Mali, Sachitanand M.,Jadhav, Sandip V.,Gopi, Hosahudya N.
supporting information; experimental part, p. 4855 - 4860 (2010/12/24)
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(ii) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
Simple and efficient synthesis of Fmoc/Boc/Cbz-protected-β-amino alcohols and peptidyl alcohols employing Boc2O
Lalithamba,Sureshbabu, Vommina V.
experimental part, p. 1372 - 1378 (2011/01/13)
An efficient method for the activation of Fmoc/Boc/Cbz-protected amino acids using Boc2O and the reduction of the in situ generated carbonic-carbonic anhydride to their corresponding 1β-amino alcohols using sodium borohydride has been described. The method is simple, rapid and free from racemization. Besides, the protocol is also extended for the conversion of N-urethane protected peptide acids to their corresponding alcohols. Copyright
Synthesis of two dipeptide isosteres containing di- and trisubstituted E-configured double bonds
Bandur, Nina G.,Harms, Klaus,Koert, Ulrich
, p. 2720 - 2730 (2008/03/12)
The stereoselective syntheses of a Tyr-Tyr and a Pro-Pro E-alkene isostere are described. While the Tyr-Tyr isostere was synthesized following a convergent olefination strategy, the trisubstituted E-configured double bond of the Pro-Pro isostere was generated by an Ireland-Claisen rearrangement. The configuration of all key intermediates containing new stereocenters was determined by X-ray crystallography. Georg Thieme Verlag Stuttgart.
First stereoselective synthesis of a Tyr-Tyr E-alkene isostere
Bandur, Nina G.,Harms, Klaus,Koert, Ulrich
, p. 99 - 102 (2008/03/13)
A stereoselective synthesis of a tyrosine-tyrosine E-alkene isostere is described. Starting from N-Fmoc-O-(tert-butyl)tyrosine as N-terminal component, the E double bond was generated by a Julia-Kocieński olefination. An enantioselective aldol reaction wa
Synthesis and biological evaluation of leucine enkephalin turn mimetics
Blomberg, David,Kreye, Paul,Fowler, Chris,Brickmann, Kay,Kihlberg, Jan
, p. 416 - 423 (2007/10/03)
A cyclic Leu-enkephalin mimetic containing a 7-membered ring, and two linear analogues, has been prepared on solid phase. In the cyclic mimetic the intramolecular (1-4) hydrogen bond found in crystalline Leu-enkephalin has been replaced by an ethylene bridge. In addition, the amide bond between Tyr1 and Gly2 has been replaced by a methylene ether isostere and Gly3 has been deleted. The two linear analogues both contain the methylene ether isostere instead of the Tyr1-Gly2 amide bond and the shorter of the two lacks Gly3. The three compounds, and a β-turn mimetic analogous to the 7-membered turn mimetic but with Gly3 included, were evaluated for specific binding to μ- and δ-opioid receptors in rat brain membranes. With the exception of the β-turn mimetic the three other Leu-enkephalin analogues all bound with varying affinity to the μ- and δ-opioid receptors. From the results it could be concluded that Leu-enkephalin binds in a turn conformation to the opiate receptors, but that this conformation is not a (1-4) β-turn. The Royal Society of Chemistry 2006.
One-pot synthesis of N-protected β-chiral amino alcohols
Somlai, Csaba,Peter, Antal,Forgo, Peter,Penke, Botond
, p. 1815 - 1820 (2007/10/03)
N-tert-butyloxycarbonyl-S-benzyl-cysteine, N-fluorenylmethyloxycarbonyl-alanine-, S-trityl-cysteine-, O-tert-butyl-serine- and O-tertbutyl-tyrosine were converted to the corresponding alcohols via sodium borohydride reduction of their in situ formed methy
