Approaches related to the synthesis of Fmoc-Ser/Thr[GalNAc(Ac) 3 -α-D]-OH DOI
Wenqiang Liu, Pan He, Shiying Shang

et al.

Journal of Carbohydrate Chemistry, Journal Year: 2023, Volume and Issue: 42(7-9), P. 223 - 251

Published: Nov. 22, 2023

Protein O-glycosylation, particularly mucin-type glycosylation, plays important biological roles. However, the limited access to homogeneously glycosylated protein isoforms (glycoforms) has impeded establishment of correlations between diverse glycan structures and properties, restricting therapeutic diagnostic applications. Chemical synthesis glycopeptides utilizing properly protected glycoamino acids as building blocks emerged a valuable approach address gap in glycoform acquisition. This review focuses on past efforts for chemical two fundamental acid blocks, Fmoc-Ser[GalNAc(Ac)3-α-D]-OH Fmoc-Thr[GalNAc(Ac)3-α-D]-OH, by categorizing various methods based glycosylation donors. The emphasis is stereoselectivity, synthetic route length, overall yield, with goal inspiring guiding future research further improve their efficiency promote advancements studies

Language: Английский

Multifunctional Lipidated Protein Carrier with a Built-In Adjuvant as a Universal Vaccine Platform Potently Elevates Immunogenicity of Weak Antigens DOI
Shihao Zhou, Ru-Yan Zhang, Yu Wen

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(8), P. 6822 - 6838

Published: April 8, 2024

Weak antigens represented by MUC1 are poorly immunogenic, which greatly constrains the development of relevant vaccines. Herein, we developed a multifunctional lipidated protein as carrier, in TLR1/2 agonist Pam3CSK4 was conjugated to N-terminus MUC1-loaded carrier BSA through pyridoxal 5′-phosphate-mediated transamination reaction. The resulting Pam3CSK4–BSA-MUC1 conjugate subsequently incorporated into liposomes, biomimics membrane structure tumor cells. results indicated that this significantly enhanced antigen uptake APCs and obviously augmented retention vaccine at injection site. Compared with BSA-MUC1 + groups, evoked 22- 11-fold increases MUC1-specific IgG titers. Importantly, elicited robust cellular immunity inhibited growth. This is first time constructed enhance immunogenicity, universal platform exhibits promise for utilization various vaccines, holding potential further clinical application.

Language: Английский

Citations

7
Synthesis of Asp-based lactam cyclic peptides using an amide-bonded diaminodiacid to prevent aspartimide formation DOI
Wenjie Li, Junyou Chen, Huixia Zhu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(18), P. 3584 - 3588

Published: Jan. 1, 2024

Asp-based lactam cyclic peptides are considered promising drug candidates. However, using Fmoc solid-phase peptide synthesis (Fmoc-SPPS) for these also causes aspartimide formation, resulting in low yields or even failure to obtain the target peptides. Here, we developed a diaminodiacid containing an amide bond as β-carboxyl-protecting group Asp avoid formation. The practicality of this has been illustrated by cyclo[Lys9,Asp13] KIIIA7-14 and 1Y.

Language: Английский

Citations

1
Semi-synthesis of Glycosylated Interferon-γ DOI

Minyuan Zhou,

Jie Zhao,

Farong Ye

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2296 - 2296

Published: Jan. 1, 2024

Language: Английский

Citations

1
Approaches related to the synthesis of Fmoc-Ser/Thr[GalNAc(Ac) 3 -α-D]-OH DOI
Wenqiang Liu, Pan He, Shiying Shang

et al.

Journal of Carbohydrate Chemistry, Journal Year: 2023, Volume and Issue: 42(7-9), P. 223 - 251

Published: Nov. 22, 2023

Protein O-glycosylation, particularly mucin-type glycosylation, plays important biological roles. However, the limited access to homogeneously glycosylated protein isoforms (glycoforms) has impeded establishment of correlations between diverse glycan structures and properties, restricting therapeutic diagnostic applications. Chemical synthesis glycopeptides utilizing properly protected glycoamino acids as building blocks emerged a valuable approach address gap in glycoform acquisition. This review focuses on past efforts for chemical two fundamental acid blocks, Fmoc-Ser[GalNAc(Ac)3-α-D]-OH Fmoc-Thr[GalNAc(Ac)3-α-D]-OH, by categorizing various methods based glycosylation donors. The emphasis is stereoselectivity, synthetic route length, overall yield, with goal inspiring guiding future research further improve their efficiency promote advancements studies

Language: Английский

Citations

0