4229-38-3Relevant articles and documents
Rapid glycoconjugation with glycosyl amines
Baudendistel, Oliver R.,Rapp, Mareike A.,Steiner, Ulrich E.,Wittmann, Valentin
, p. 14901 - 14906 (2021/12/02)
Conjugation of unprotected carbohydrates to surfaces or probes by chemoselective ligation reactions is indispensable for the elucidation of their numerous biological functions. In particular, the reaction with oxyamines leading to the formation of carbohydrate oximes which are in equilibrium with cyclic N-glycosides (oxyamine ligation) has an enormous impact in the field. Although highly chemoselective, the reaction is rather slow. Here, we report that the oxyamine ligation is significantly accelerated without the need for a catalyst when starting with glycosyl amines. Reaction rates are increased up to 500-fold compared to the reaction of the reducing carbohydrate. For comparison, aniline-catalyzed oxyamine ligation is only increased 3.8-fold under the same conditions. Glycosyl amines from mono- and oligosaccharides are easily accessible from reducing carbohydrates via the corresponding azides by using Shoda's reagent (2-chloro-1,3-dimethylimidazolinium chloride, DMC) and subsequent reduction. Furthermore, glycosyl amines are readily obtained by enzymatic release from N-glycoproteins making the method suited for glycomic analysis of these glycoconjugates which we demonstrate employing RNase B. Oxyamine ligation of glycosyl amines can be carried out at close to neutral conditions which makes the procedure especially valuable for acid-sensitive oligosaccharides. This journal is
A Tripeptide Approach to the Solid-Phase Synthesis of Peptide Thioacids and N-Glycopeptides
Sch?we, Markus Julian,Keiper, Odin,Unverzagt, Carlo,Wittmann, Valentin
, p. 15759 - 15764 (2019/11/19)
A general and robust method for the incorporation of aspartates with a thioacid side chain into peptides has been developed. Pseudoproline tripeptides served as building blocks for the efficient fluorenylmethyloxycarbonyl (Fmoc) solid-phase synthesis of t
Convergent Synthesis of N-Linked Glycopeptides via Aminolysis of ω-Asp p-Nitrophenyl Thioesters in Solution
Du, Jing-Jing,Gao, Xiao-Fei,Xin, Ling-Ming,Lei, Ze,Liu, Zheng,Guo, Jun
supporting information, p. 4828 - 4831 (2016/10/14)
An efficient N-linked glycosylation reaction between glycosylamines and p-nitrophenyl thioester peptides has been developed. The reaction conditions are mild and compatible with the C-terminal free carboxylic acid group and the unprotected N-linked sialyl