Tarbe, Marion, Azcune, Itxaso, Balentová, Eva, Miles, John J., Edwards, Emily E., Miles, Kim M., Do, Priscilla, Baker, Brian M., Sewell, Andrew K., Aizpurua, Jesus M., Douat-Casassus, Céline, and Quideau, Stéphane (2010) Design, synthesis and evaluation of β-lactam antigenic peptide hybrids; unusual opening of the β-lactam ring in acidic media. Organic and Biomolecular Chemistry, 8 (23). pp. 5345-5353.

PDF (Published Version) - Published Version Restricted to Repository staff only

Abstract

β-Lactam peptides were envisioned as conformational constraints in antigenic peptides (APs). Three different β-lactam tripeptides of varying flexibility were prepared in solution and incorporated in place of the central part of the altered melanoma associated antigenic peptide Leu₂₇-Melan-A₂₆₋₃₅ using solid phase synthesis techniques. Upon TFA cleavage from the solid support, an unexpected opening of the β-lactam ring occurred with conservation of the amide bond. After adaptation of the solid phase synthesis strategy, β-lactam peptides were successfully obtained and both opened and closed forms were evaluated for their capacity to bind to the antigen-presenting class-I MHC HLA-A2 protein system. None of the closed β-lactam peptides bound to HLA-A2, but their opened variants were shown to be moderate to good HLA-A2 ligands, one of them being even capable of stimulating a Melan-A-specific T cell line.

Item ID:	45236
Item Type:	Article (Research - C1)
ISSN:	1477-0539
Funders:	Société Française de Chimie Thérapeutique (SFCT), Ministerio de Educación y Ciencia (MEC), Gobierno Vasco (GV), National Health and Medical Research Council (NHMRC)
Projects and Grants:	MEC Grant CTQ2006-13891/BQU, GV ETORTEK inanoGUNE IE-08/225
Date Deposited:	06 Sep 2016 22:43
FoR Codes:	11 MEDICAL AND HEALTH SCIENCES > 1107 Immunology > 110702 Applied Immunology (incl Antibody Engineering, Xenotransplantation and T-cell Therapies) @ 100%
SEO Codes:	92 HEALTH > 9201 Clinical Health (Organs, Diseases and Abnormal Conditions) > 920108 Immune System and Allergy @ 100%
Downloads:	Total: 6
	More Statistics