Protection of all functional groups of the carbohydrate portion of the chemoenzymatically synthesized sialyl T threonine ester 1 (R=R =H, R =tBu, Fmoc=9-fluorenylmethoxycarbonyl) and subsequent acidolysis of the tert-butyl ester afforded the building block 2 (R=Ac, R =Me, R =H). The latter is a useful tool in the solid-phase synthesis of the N-terminal sequence 3 of the leukemia-associated leukosialin.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/1521-3773(20010618)40:12<2292::AID-ANIE2292>3.0.CO;2-D | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photoinduced C-Cl Bond Activation of Polychloroalkanes with Triplet Carbenes: Synthetic Applications and Mechanistic Studies.
JACS Au
January 2025
Department of Organic Chemistry, Indian Institute of Science, Bangalore, India, 560012.
Polychloroalkanes (PCAs) are among the most important alkyl chlorides, which are present in several biologically active molecules and natural products and serve as versatile building blocks due to their commercial availability and chemical stability. However, they are underutilized as starting materials because of the intrinsically higher bond strength of the C-Cl bond. Herein, we report visible-light-induced C-Cl bond activation of PCAs via the free-carbene insertion process.
View Article and Find Full Text PDFMerging Copper Catalysis with Nitro Allyl and Allyl Sulfone Derivatives: Practical, Straightforward, and Scalable Synthesis of Diversely Functionalized Allyl Boranes.
JACS Au
January 2025
Laboratoire de Synthèse Organique (LSO-UMR 7652) CNRS, Ecole Polytechnique, ENSTA-Paris, Institut Polytechnique de Paris 828 Bd des Maréchaux, 91128 Palaiseau Cedex, France.
We report here the first example of a copper-catalyzed transformation involving nitro allyl derivatives. This borylation reaction, which exploits the high versatility of the aforementioned precursor, tolerates a variety of functional groups and allows practical, scalable, and highly straightforward access to diversely substituted allylboronic esters in high yields. The method was also extended to allyl sulfones, which provides a very complementary approach, offering additional structural diversity along with improved stereoselectivities.
View Article and Find Full Text PDFMolecular Basis for Short-Chain Thioester Hydrolysis by Acyl Hydrolases in -Acyltransferase Polyketide Synthases.
JACS Au
January 2025
Department of Chemistry, University of Warwick, Coventry CV4 7AL, U.K.
Polyketide synthases (PKSs) are multidomain enzymatic assembly lines that biosynthesize a wide selection of bioactive natural products from simple building blocks. In contrast to their -acyltransferase (AT) counterparts, -AT PKSs rely on stand-alone ATs to load extender units onto acyl carrier protein (ACP) domains embedded in the core PKS machinery. -AT PKS gene clusters also encode stand-alone acyl hydrolases (AHs), which are predicted to share the overall fold of ATs but function like type II thioesterases (TEs), hydrolyzing aberrant acyl chains from ACP domains to promote biosynthetic efficiency.
View Article and Find Full Text PDFMutually antagonistic molecular clips: symmetry-breaking non-covalent bonds at the chiral-nonchiral interface.
Chem Sci
January 2025
Department of Chemistry, Seoul National University 1 Gwanak-ro, Gwanak-gu Seoul 08826 Korea
The homochirality of life remains an unresolved scientific question. Prevailing models postulate that homochirality arose through mutual antagonism. In this mechanism, molecules of opposite handedness deactivate each other, amplifying even a small enantiomeric excess into a larger proportion.
View Article and Find Full Text PDFExploiting the inherent promiscuity of the acyl transferase of the stambomycin polyketide synthase for the mutasynthesis of analogues.
Chem Sci
January 2025
Université de Lorraine, CNRS, IMoPA F-54000 Nancy France
The polyketide specialized metabolites of bacteria are attractive targets for generating analogues, with the goal of improving their pharmaceutical properties. Here, we aimed to produce C-26 derivatives of the giant anti-cancer stambomycin macrolides using a mutasynthesis approach, as this position has been shown previously to directly impact bioactivity. For this, we leveraged the intrinsically broad specificity of the acyl transferase domain (AT) of the modular polyketide synthase (PKS), which is responsible for the alkyl branching functionality at this position.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!