160168-40-1Relevant articles and documents
Improving Selectivity, Proteolytic Stability, and Antitumor Activity of Hymenochirin-1B: A Novel Glycosylated Staple Strategy
Li, Yulei,Zhang, Yihan,Wu, Minghao,Chang, Qi,Hu, Honggang,Zhao, Xia
, p. 516 - 525 (2019/03/11)
As a host defense peptide, hymenochirin-1B has attracted increasing attention for its strong cytotoxic activities. However, its poor selectivity and proteolytic stability remain major obstacles for clinical application. To solve these problems, we designed and synthesized a series of peptide analogues of hymenochirin-1B based on cationic residue substitution and stapling combined with a glycosylation strategy. Some analogues showed improvement not only in selectivity and proteolytic stability but also in antitumor activity. Among them, the glycosylated stapled peptide H-58 was identified as the most potential antitumor peptide. Flow cytometry and a competitive binding assay revealed that H-58 displayed significant antitumor selectivity. Confocal microscopy and nuclear staining with Hoechst dye demonstrated that H-58 entered the nucleus and caused DNA damage. In summary, the strategy of glycosylated stapled peptides is a promising approach for improving the antitumor selectivity, proteolytic stability, and antitumor activity of hymenochirin-1B, which can be used for other bioactive peptide modifications.
Simple and Efficient Preparation of O- and S-GlcNAcylated Amino Acids through InBr3-Catalyzed Synthesis of β- N-Acetylglycosides from Commercially Available Reagents
De Leon, Cesar A.,Lang, Geoffrey,Saavedra, Marcos I.,Pratt, Matthew R.
supporting information, p. 5032 - 5035 (2018/08/24)
The facile synthesis of serine, threonine, and cysteine β-glycosides using commercially available peracetylated β-N-acetylglucosamine (β-Ac4GlcNAc) and catalytic amounts of indium bromide (InBr3) is described. This method involves only inexpensive reagents that require no further modification or special handling. The reagents are simply mixed, dissolved, and refluxed to afford the GlcNAcylated amino acids in great yields (70-80%). This operationally simple procedure should facilitate the study of O-GlcNAcylation without necessitating expertise in synthetic carbohydrate chemistry.
Divergent behavior of glycosylated threonine and serine derivatives in solid phase peptide synthesis
Zhang, Yalong,Muthana, Saddam M.,Barchi, Joseph J.,Gildersleeve, Jeffrey C.
supporting information; experimental part, p. 3958 - 3961 (2012/10/18)
Solid phase peptide coupling of glycosylated threonine derivatives was systematically evaluated. In contrast to glycosylated serine derivatives which are highly prone to epimerization, glycosylated threonine derivatives produce only negligible amounts of epimerization. Under forcing conditions, glycosylated threonine analogs undergo β-elimination, rather than epimerization. Mechanistic studies and molecular modeling were used to understand the origin of the differences in reactivity. This article not subject to U.S. Copyright. Published 2012 by the American Chemical Society.
Practical synthesis of the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucosides of Fmoc-serine and Fmoc-threonine and their benzyl esters
Carvalho, Ivone,Scheuerl, Shona L.,Kartha, K.P. Ravindranathan,Field, Robert A.
, p. 1039 - 1043 (2007/10/03)
Mercuric bromide-promoted glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl chloride in refluxing 1,2-dichloroethane gave the corresponding β-glycosides in good yields (64 and 62%, respectively).
Building Blocks for Solid-phase Glycopeptide Synthesis: 2-Acetamido-2-deoxy-β-D-glycosides of FmocSerOH and FmocThrOH
Arsequell, Gemma,Krippner, Lorely,Dwek, Raymond A.,Wong, Simon Y. C.
, p. 2383 - 2384 (2007/10/02)
A convenient and optimized synthesis of 2-acetamido-2-deoxy-β-D-glycosides of FmocSerOH and FmocThrOH, building blocks for solid-phase synthesis of glycopeptides containing GlcNAc β-linked to Ser or Thr, is for the first time established.
