108963-96-8Relevant articles and documents
Total Synthesis of Malacidin A by β-Hydroxyaspartic Acid Ligation-Mediated Cyclization and Absolute Structure Establishment
Brady, Sean F.,Chen, Sheng,Forelli, Nicholas,Li, Xuechen,Po, Kathy Hiu Laam,Shang, Zhuo,Sun, Zhenquan
, p. 19868 - 19872 (2020)
The development of novel antibiotics is critical to combating the growing emergence of drug-resistant pathogens. Malacidin A is a new member of the calcium-dependent antibiotic (CDAs) family with activity against antibiotic-resistant pathogens. Its mode of action is distinct from classical CDAs. However, the absolute structure of malacidin A has not been established. Herein, the total syntheses of malacidin A and its analogues are reported by a combination of Fmoc-based solid-phase peptide synthesis (SPPS) and β-hydroxyaspartic acid ligation-mediated peptide cyclization. The total synthesis enabled us to establish the absolute configuration of malacidin A, which is in agreement with those for natural malacidin A confirmed by advanced Marfey's analysis in our study.
A convenient and efficient synthesis of (2S,4R)- and (2S,4S)-4-methylglutamic acid
Coudert, Elisabeth,Acher, Francine,Azerad, Robert
, p. 863 - 865 (1997)
Both enantiomerically pure (2S,4S)- and (2S,4R)-4-methylglutamic acids have been prepared in an overall 60% yield, by a convenient 7-step synthesis based on C-4 alkylation/epimerization of readily available (S)-pyroglutamic acid.
Synthesis of a new chiral amine: (S)-5,5-dimethyl-2-methoxymethyl-pyrrolidine
Brena-Valle,Cruz-Almanza,Guadarrama-Morales
, p. 697 - 706 (2001)
The title compound, a potential 'quat' auxiliary,was prepared from (S)-glutamic acid derivatives like (S)-N-Benzyl-5-methoxymethyl-2-pyrrolidinone 1. Other routes starting from (S)-pyroglutamic acid in an attempt to bypass N-Aryl compounds like 1 were also tested, but have not rendered the expected results yet.
Preparation of peptide-like bicyclic lactams via a sequential Ugi reaction - Olefin metathesis approach
Krelaus, Ralf,Westermann, Bernhard
, p. 5987 - 5990 (2004)
Bicyclic lactams, suitable for incorporation into conformationally restricted peptide mimics, can be synthesized by using olefinic starting materials for the Ugi multicomponent reaction, setting up an olefin metathesis reaction, that is easily carried out with the Grubbs catalyst. The influence of the different starting materials is evaluated. In addition, the utilization of chiral, nonracemic amines is described.
An cost-effective and safe process of L-cis-4,5-methanoproline amide, the key synthetic intermediate of saxagliptin, via an improved Simmons-Smith reaction
Ding, Ding,Pan, Xianhua,Yu, Wansheng,Li, Xiaojun,Chen, Suke,Liu, Feng
, p. 719 - 726 (2015)
L-cis-4,5-Methanoproline amide, a key intermediate of saxagliptin, was synthesized by an improved Simmons-Smith reaction. The zinc carbenoid was formed through Zn/CuBr and CH2I2, under the optimized condition, the title compound was gained with 68% yield and excellent diastereomeric selectivity (40:1 d.r.). The absence of the flammable and expensive ZnEt2 makes this procedure very attractive in large scale production.
Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry
Sanchez, Clément A.,Gadais, Charlène,Chaume, Grégory,Girard, Sylvaine,Chelain, Evelyne,Brigaud, Thierry
supporting information, p. 382 - 387 (2021/01/13)
The straightforward synthesis of enantiopure 5-(R)-and 5-(S)-trifluoromethylproline is reported. The key steps are a Ruppert-Prakash reagent addition on l-pyroglutamic esters followed by an elimination reaction and a selective reduction. The solution-phase and solid-phase incorporation of this unprotected enantiopure fluorinated amino acid in a short peptide chain was demonstrated. Compared to proline, the CF3 group provides a decrease of the trans to cis amide bond isomerization energy and an increase of the cis conformer population.
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Paragraph 00463; 00470-00471, (2021/10/15)
Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.