70642-86-3Relevant articles and documents
Total Synthesis and Bioactivity Mapping of Geodiamolide H
Arndt, Hans-Dieter,B??neck, Johanna,Bellstedt, Peter,Dahse, Hans-Martin,G?rls, Helmar,Küllmer, Florian,Nasufovi?, Veselin,Stallforth, Pierre
supporting information, p. 11633 - 11642 (2021/07/02)
The first total synthesis of the actin-stabilizing marine natural product geodiamolide H was achieved. Solid-phase based peptide assembly paired with scalable stereoselective syntheses of polyketide building blocks and an optimized esterification set the
Semisynthesis of a Bacterium with Non-canonical Cell-Wall Cross-Links
Chen, Jason S.,Dik, David A.,Schultz, Peter G.,Webb, Bill,Zhang, Nan
supporting information, p. 10910 - 10913 (2020/07/08)
The cell wall is an elaborate framework of peptidoglycan that serves to protect the bacterium against osmotic challenge. This exoskeleton is composed of repeating saccharides covalently cross-linked by peptide stems. The general structure of the cell wall is widely conserved across diverse Gram-negative bacteria. To begin to explore the biological consequence of introducing non-canonical cross-links into the cell wall of Escherichia coli, we generated a bacterium where up to 31percent of the cell-wall cross-links are formed by a non-enzymatic reaction between a sulfonyl fluoride and an amino group. Bacteria with these non-canonical cell-wall cross-links achieve a high optical density in culture, divide and elongate successfully, and display no loss of outer membrane integrity. This work represents a first step in the design of bacteria with non-canonical "synthetic"cell walls.
Total Synthesis of Herquline B and C
Cox, Joshua B.,Kimishima, Aoi,Wood, John L.
supporting information, p. 25 - 28 (2019/01/16)
The total syntheses of (-)-herquline B (2) and a heretofore-unrecognized congener, (+)-herquline C (3), are described. The syntheses require 14 and 13 steps, respectively, and feature a key oxazoline reduction that sets the stage for piperazine construction.
Synthesis of Majusculamides A and B
Nakajima, Daisuke,Sueyoshi, Kosuke,Orihara, Kensuke,Teruya, Toshiaki,Yokoshima, Satoshi
supporting information, p. 924 - 927 (2019/05/10)
The synthesis of two marine lipodipeptides, majusculamides A and B, is described. The key feature of this synthesis is the stereoselective construction of an α-methyl-β-keto-carboxamide moiety.
Asymmetric solution-phase mixture aldol reaction using oligomeric ethylene glycol tagged chiral oxazolidinones
Turkyilmaz, Serhan,Wilcox, Craig S.
supporting information, p. 2031 - 2033 (2017/05/04)
Sorting tags are oligomeric structures that can be used as protecting groups or chiral auxiliaries enabling solution-phase mixture syntheses of multiple tagged compounds in one pot and allowing for facile and predictable chromatographic separation of products at the end of synthetic sequences. Perfluorinated hydrocarbon and oligomeric ethylene glycol (OEG) derivatives are known classes of sorting tags. Herein we describe the preparation of OEGylated chiral oxazolidinones and their use in asymmetric solution-phase mixture aldol reactions. Through the use of such oxazolidinones based on tyrosine four different individually tagged aldol adducts were obtained as a mixture, chromatographically demixed, detagged, and it was shown that these processes gave the desired aldol products in good yield and enantioselectivity.
Rational design of a redox-labeled chiral target for an enantioselective aptamer-based electrochemical binding assay
Moreau, Julie,Challier, Lylian,Lalaoui, Noemie,Mavre, Francois,Noel, Vincent,Limoges, Benoit,Schoellhorn, Bernd,Fave, Claire
supporting information, p. 2953 - 2959 (2014/03/21)
A series of redox-labeled L-tyrosinamide (L-Tym) derivatives was prepared and the nature of the functional group and the chain length of the spacer were systematically varied in a step-by-step affinity optimization process of the tracer for the L-Tym aptamer. The choice of the labeling position on L-Tym proved to be crucial for the molecular recognition event, which could be monitored by cyclic voltammetry and is based on the different diffusion rates of free and bound targets in solution. From this screening approach an efficient electroactive tracer emerged. Comparable dissociation constants Kd were obtained for the unlabeled and labeled targets in direct or competitive binding assays. The enantiomeric tracer was prepared and its enantioselective recognition by the corresponding anti-D-Tym aptamer was demonstrated. The access to both enantiomeric tracer molecules opens the door for the development of one-pot determination of the enantiomeric excess when using different labels with well-separated redox potentials for each enantiomer. Trace compounds: Redox tracers have been synthesized for enantioselective electrochemical ligand binding assays by relying on the combined use of an oligonucleotide-aptamer receptor with the detection of the redox label. A rational step-by-step optimization procedure has been developed leading to a redox-labeled L-tyrosinamide derivative (see figure) conserving the high affinity towards the aptamer.
Tyrosine-based 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine and -adenine ((S)-HPMPC and (S)-HPMPA) prodrugs: Synthesis, stability, antiviral activity, and in vivo transport studies
Zakharova, Valeria M.,Serpi, Michaela,Krylov, Ivan S.,Peterson, Larryn W.,Breitenbach, Julie M.,Borysko, Katherine Z.,Drach, John C.,Collins, Mindy,Hilfinger, John M.,Kashemirov, Boris A.,McKenna, Charles E.
experimental part, p. 5680 - 5693 (2011/10/18)
Eight novel single amino acid (6-11) and dipeptide (12, 13) tyrosine P-O esters of cyclic cidofovir ((S)-cHPMPC, 4) and its cyclic adenine analogue ((S)-cHPMPA, 3) were synthesized and evaluated as prodrugs. In vitro IC 50 values for the prodrugs (50 0.3-35 μM); there was no cytoxicity with KB or HFF cells at ≤100 μM. The prodrugs exhibited a wide range of half-lives in rat intestinal homogenate at pH 6.5 (30-1732 min) with differences of 3-10× between phostonate diastereomers. The tyrosine alkylamide derivatives of 3 and 4 were the most stable. (l)-Tyr-NH-i-Bu cHPMPA (11) was converted in rat or mouse plasma solely to two active metabolites and had significantly enhanced oral bioavailability vs parent drug 1 in a mouse model (39% vs 5%).
Suppression of racemization in the carbonylation of amino acid-derived aryl triflates
Grimm, Jonathan B.,Wilson, Kevin J.,Witter, David J.
, p. 4509 - 4513 (2008/02/03)
The carbonylation of enantiopure phenylglycine-derived aryl triflates was achieved to afford 4-carboxyphenylglycine analogs with high enantiomeric excesses (88 to >99% ee). Amide analogs of phenylglycine were well-tolerated in the hydroxy- and methoxycarbonylation processes, providing efficient access to benzoic acid and ester building blocks. The % ee of the product was dependent on the relative steric bulk of both the amino acid substrate and the requisite amine base, with iPr2NEt proving optimal in minimizing product racemization.
Hydroxyphenyl derivatives with HIV integrase inhibitory properties
-
, (2008/06/13)
An hydroxyphenyl derivative selected from the group consisting of a compound of formula and when a compound of formula I comprises a carboxylic acid group pharmaceutically acceptable salts thereof and when a compound of formula I comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein n is 1, 2 or 3, e is 1, 2 or 3, Hal represents a halogen atom (e.g. Cl, Br, F or I), p is 0, 1 or 2, r is 0, 1 or 2, X and X′ each independently represents a single bond, a saturated straight or branched hydrocarbon group of 1 to 4 carbon atoms or a straight or branched hydrocarbon group of 2 to 4 carbon atoms comprising a carbon to carbon double bond, Rarepresents H or —CH3, and Raarepresents H or —CH3; W may represent an amino acid residue or fragment. These compounds may be used to inhibit the activity of HIV integrase.
An efficient synthesis of (-)-deacetylanisomycin starting from D-tyrosine1
Chandrasekhar,Ramachandar,Venkat Reddy
, p. 1867 - 1870 (2007/10/03)
The antibiotic (-)-deacetylanisomycin was synthesized starting from D-tyrosine using Sharpless asymmetric dihydroxylation as a key reaction.
