114396-63-3Relevant academic research and scientific papers
An efficient enantioselective synthesis of (S)-α-methyl-serine methyl ester hydrochloride via asymmetrically catalyzed amination
Xiao, Qiong,Tang, Yi-Fan,Xie, Ping
, p. 61 - 68 (2020)
We present the synthesis of enantiomerically pure (S)-α-methyl-serine methyl ester hydrochloride from 2-methyl-3-((4-(trifluoromethyl)benzyl)oxy)propanal and di-p-chlorobenzyl azodicarboxylate via asymmetrically catalyzed amination with naphthylalanine de
Total Synthesis of Tambromycin by Combining Chemocatalytic and Biocatalytic C?H Functionalization
Zhang, Xiao,King-Smith, Emma,Renata, Hans
, p. 5037 - 5041 (2018)
A combination of genomic and metabolomic approaches recently resulted in the identification of a nonribosomal tetrapeptide tambromycin, which possesses promising antiproliferative activity and several unusual structural features, including a densely substituted indole, a methyloxazoline ring, and an unusual pyrrolidine-containing amino acid called tambroline. In this work, we identify a concise synthetic route to access tambromycin, which relies on the strategic use of biocatalytic and chemocatalytic C?H functionalization methods to prepare two key precursors to the natural product in an efficient and scalable manner. The success of our study highlights the benefits of applying the principles of biocatalytic retrosynthesis as well as C?H functionalization logic to the synthesis of complex molecular scaffolds.
Total Synthesis of Mycobacterium tuberculosis Dideoxymycobactin-838 and Stereoisomers: Diverse CD1a-Restricted T Cells Display a Common Hierarchy of Lipopeptide Recognition
Cheng, Janice M. H.,Liu, Ligong,Pellicci, Daniel G.,Reddiex, Scott J. J.,Cotton, Rachel N.,Cheng, Tan-Yun,Young, David C.,Van Rhijn, Ildiko,Moody, D. Branch,Rossjohn, Jamie,Fairlie, David P.,Godfrey, Dale I.,Williams, Spencer J.
supporting information, p. 1694 - 1701 (2017/02/10)
Mycobacterium tuberculosis produces dideoxymycobactin-838 (DDM-838), a lipopeptide that potently activates T cells upon binding to the MHC-like antigen-presenting molecule CD1a. M. tuberculosis produces DDM-838 in only trace amounts and a previous solid-phase synthesis provided sub-milligram quantities. We describe a high-yielding solution-phase synthesis of DDM-838 that features a Mitsunobu substitution that avoids yield-limiting epimerization at lysine during esterification, and amidation conditions that prevent double-bond isomerization of the Z-C20:1 acyl chain, and provides material with equivalent antigenicity to natural DDM-838. Isomers of DDM-838 that varied in stereochemistry at the central lysine and the C20:1 acyl chain were compared for their ability to be recognised by CD1a-restricted T cell receptors (TCRs). These TCRs, derived from unrelated human donors, exhibited a similar spectrum of reactivity towards the panel of DDM-838 isomers, highlighting the exquisite sensitivity of lipopeptide-reactive T cells for the natural DDM stereochemistry.
Catalytic enantioselective electrophilic aminations of acyclic α-alkyl β-carbonyl nucleophiles
Liu, Xiaofeng,Sun, Bingfeng,Deng, Li
scheme or table, p. 1685 - 1689 (2009/12/06)
Highly enantioselective aminations of acyclic α-alkyl β-keto thioesters and trifluoroethyl α-methyl α-cyanoacetate (12) with as low as 0.05 mol% of a bifunctional cinchona alkaloid catalyst were established. This ability to afford high enantioselectivity
ASYMMETRIC ALDOL REACTION OF α-ISOCYANOCARBOXYLATES WITH PARAFORMALDEHYDE CATALYZED BY CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEXES: CATALYTIC ASYMMETRIC SYNTHESIS OF α-ALKYLSERINES
Ito, Yoshihiko,Sawamura, Masaya,Shirakawa, Eiji,Hayashizaki, Keiichi,Hayashi, Tamio
, p. 235 - 238 (2007/10/02)
Aldol reaction of methyl α-isocyanocarboxylates (CNCH(R)COOMe: R=H, Me, Et, i-Pr, Ph) with paraformaldehyde in the presence of 1 molpercent of a chiral (aminoalkyl)ferrocenylphosphine-gold(I) complex gave optically active 4-alkyl-2-oxazoline-4-carboxylates (up to 83percent ee) which were readily hydrolyzed to α-alkylserines.
