162523-77-5Relevant academic research and scientific papers
Glucose-conjugated platinum(IV) complexes as tumor-targeting agents: design, synthesis and biological evaluation
Wang, Haifeng,Yang, Xiande,Zhao, Caili,Wang, Peng George,Wang, Xin
, p. 1639 - 1645 (2019)
A new series of glucose-conjugated Pt(IV) complexes that target tumor-specific glucose transporters (GLUTs) was designed, synthesized, and evaluated for their anticancer activities. All six compounds, namely, A1-A6, exhibited increased cytotoxicity that w
Design and synthesis of a novel class of sugar-peptide hybrids: C-linked glyco β-amino acids through a stereoselective "acetate" Mannich reaction as the key strategic element
Palomo, Claudio,Oiarbide, Mikel,Landa, Aitor,Gonzalez-Rego, M. Concepcion,Garcia, Jesus M.,Gonzalez, Alberto,Odriozola, Jose M.,Martin-Pastor, Manuel,Linden, Anthony
, p. 8637 - 8643 (2007/10/03)
A new type of sugar-amino acid hybrid, which is comprised of a sugar unit (gluco-, galacto-, or mannopyranose) linked through a C-glycosidic linkage to the β-position of an α-unsubstituted β-amino acid unit, is presented. It is hypothesized that these new compounds, or the oligomeric peptides derived therefrom, might possess the structural features of β-amino acid oligomers and the chemical and enzymatic resistance of C-glycosides to hydrolysis. The synthetic strategy is based on a new Mannich-type reaction between a chiral acetate enolate equivalent and α-amido sulfones derived from the corresponding sugar-C-glycoside aldehydes. While the sugar-C-glycoside aldehyde partner is prepared from well-established transformations on known sugar precursors, the lithium enolate derived from (1 R)-endo-2-acetylisoborneol 3 is employed as the key element. This Mannich approach proceeds with essentially perfect diasteromeric control leading to the new β-amino carbonyl adducts in good yields. Further, cleavage of the camphor auxiliary is smoothly performed by oxidative treatment with ammonium cerium nitrate (CAN). Complementarily, direct peptide-type coupling of the β-amino carbonyl Mannich adducts with an α- or β-amino acid residue and subsequent CAN-promoted detachment of the auxiliary yields dipeptide fragments bearing a sugar-containing aliphatic side chain and is a process that can be iterated. A preliminary conformational study based on the combination of experimental NMR data and molecular mechanics and molecular dynamics (MD) of one particular adduct is also provided.
Strategies for the synthesis of C-disaccharides containing D and L sugars
Armstrong, Robert W.,Sutherlin, Daniel P.
, p. 7743 - 7746 (2007/10/02)
The osmylation of C-1 homologated diene ester monosaccharides readily affords C-disaccharides of diverse but predictable stereochemistry. As an example, D-glu-α(1,6)-D-gal(3), D-glu-α(1,6)-L-gal(4), D-glu-α(1,6)-D-ido (10), and D-glu-α(1,6)-L-ido (11) wer
