213675-13-9Relevant academic research and scientific papers
Sweet and salted: Sugars meet hydroxyapatite
Sandri, Monica,Natalello, Antonino,Bini, Davide,Gabrielli, Luca,Cipolla, Laura,Nicotra, Francesco
supporting information; experimental part, p. 1845 - 1848 (2011/10/01)
Carbonated hydroxyapatite (CHA) has been successfully biodecorated with carbohydrate derivatives, via silylation of the hydroxy groups of the apatite and subsequent covalent bonding with a suitably functionalized carbohydrate moiety. The presented procedu
Facile preparation of an orthogonally protected, pH-sensitive, bioconjugate linker for therapeutic applications
Fletcher, Steven,Jorgensen, Michael R.,Miller, Andrew D.
, p. 4245 - 4248 (2007/10/03)
(Chemical Equation Presented) We describe the facile, three-step synthesis of an orthogonally protected, pH-sensitive linker (8), based on maleic acid, and report its application to the preparation of a pH-sensitive phospholipid (20) for potential use in drug and gene delivery. In addition, we highlight the benefits of our linker over the use of the commercially available cis-aconitic anhydride (4).
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.
Differential carbohydrate recognition of two GlcNAc-6-sulfotransferases with possible roles in L-selectin ligand biosynthesis
Cook, Brian N.,Bhakta, Sunil,Biegel, Teresa,Bowman, Rendra G.,Armstrong, Joshua I.,Hemmerich, Stefan,Bertozzi, Carolyn R.
, p. 8612 - 8622 (2007/10/03)
Two human GlcNAc-6-sulfotransferases, CHST2 and HEC-GlcNAc6ST, have been recently identified as possible contributors to the inflammatory response by virtue of their participation in L-selectin ligand biosynthesis. Selective inhibitors would facilitate their functional elucidation and might provide leads for antiinflammatory therapy. Here we investigate the critical elements of a disaccharide substrate that are required for recognition by CHST2 and HEC-GlcNAc6ST. A panel of disaccharide analogues, bearing modifications to the pyranose rings and aglycon substituents, were synthesized and screened for substrate activity with each enzyme. Both GlcNAc-6-sulfotransferases required the 2-N-acetamido and 4-hydroxyl groups of a terminal GlcNAc residue for conversion to product. Both enzymes tolerated modifications to the reducing terminal pyranose. Key differences in recognition of an amide group in the aglycon substituent were observed, providing the basis for future glycomimetic inhibitor design.
Remote asymmtric induction: Synthesis of C-linked α-galactoserine and homoserine derivatives by electrophilic amination
Arya, Prabhat,Ben, Robert N.,Qin, Huiping
, p. 6131 - 6134 (2007/10/03)
A high diastereoselectivity (98%) for electrophilic of compound 9 using di-t-butyl azodicarboxyl ester as an electrophile was achieved. A similar reaction with compound 13 having achiral oxazolidinone was studied to examine 1,4-remote asymmetric induction. In the latter, a selectivity of 6.5:1 demonstrated the effect of α-galactosyl moiety, responsible for inducing the induction from the remote site.
