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.
Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix conformation
Aillard, Boris,Kilburn, Jeremy D.,Blaydes, Jeremy P.,Tizzard, Graham J.,Findlow, Stuart,Werner, J?rn M.,Bloodworth, Sally
, p. 4562 - 4569 (2015)
We describe the development of a small-molecule mimic of Xaa-trans-Pro dipeptide in poly-l-proline type II helix conformation, based upon a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane core structure. Stereoselective synthesis of the mimic from l-pyroglutamic acid is achieved in twelve linear steps and 9.9% yield. Configurational and conformational analyses are conducted using a combination of 1H NMR spectroscopy, X-ray crystallography and circular dichroism spectroscopy; and evaluation of the mimic as a promising surrogate dipeptide, in a protein-protein interaction between the SH3 domain of human Fyn kinase (Fyn SH3) and peptidomimetics of its biological ligand, are conducted by 1H-15N HSQC NMR titration experiments.
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.
A versatile chiral pyrrolidine aldehyde building-block for synthesis and formal synthesis of ent-nakadomarin A
Stockman, Robert A.,McDermott, Paul J.,Newton, Annabella F.,Magnus, Philip
, p. 559 - 562 (2010)
A stable, simple to synthesise and versatile chiral aldehyde building-block has been developed, its reactivity in Wittig, Horner-Wadsworth-Emmons and Grignard reactions investigated, and its use is demonstrated in a highly efficient synthesis of an intermediate in Dixon's synthesis of nakadomarin A. Georg Thieme Verlag Stuttgart.
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.
Separation of pyrrolidine allylation products by diastereoselective enzymatic ester hydrolysis
Aggarwal, Varinder K.,Astle, Christopher J.,Iding, Hans,Wirz, Beat,Rogers-Evans, Mark
, p. 945 - 947 (2005)
A multi-parallel enzyme screen has been used to identify potential catalysts for the selective hydrolysis of diastereomeric esters and then subsequently applied in their separation upon scaleup.
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.
Oxidation of α-amino acids promoted by the phthalimide N-oxyl radical: A kinetic and product study
Ticconi, Barbara,Mazzonna, Marco,Lanzalunga, Osvaldo,Lapi, Andrea
, p. 3579 - 3585 (2019)
A kinetic study of the hydrogen atom transfer (HAT) reaction from a series of N-Boc- or N-Acetyl-protected amino acids to the phthalimide N-oxyl radical (PINO) was carried out to obtain information about reactivity and selectivity patterns. With amino acids containing aliphatic side chains, the 2nd order rate constants are of the same order of magnitude, in agreement with a HAT process involving the Cα?H bond. Proline is the most reactive substrate suggesting that HAT process involves the Cδ?H bond instead of Cα?H bond. These results are confirmed by the product analysis of the aerobic oxidations of the corresponding N-Boc and N-Ac protected amino acids methyl esters promoted by N-hydroxyphthalimide. Comparison of our results with those reported for HAT reactions to other radical species indicates that PINO displays electrophilic characteristics that are intermediate between those observed for the more stable Br[rad] radical and the more reactive cumyloxyl radical.
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.
Synthesis of (2S,3S)-[3-2H1]- and (2S,3R)-[2,3-2H2]-proline
Dieterich,Young
, p. 5455 - 5458 (1993)
Discovery of conditions for intramolecular trapping of a ketene intermediate has led to an effective synthesis of samples of the amino acid proline which are stereospecifically labelled on the β-carbon. Since samples of stereospecifically labelled pyroglutamic acid derivatives are prepared in the route, other stereospecifically labelled, biologically important amino acids may be accessed by the synthesis.
