Synthesis of Tn, sialyl Tn and HIV-1-derived peptide antigen conjugates having a lipid A analog as an immunoadjuvant for synthetic vaccines

K Miyajima; T Nekado; K Ikeda; K Achiwa

doi:10.1248/cpb.46.1676

Synthesis of Tn, sialyl Tn and HIV-1-derived peptide antigen conjugates having a lipid A analog as an immunoadjuvant for synthetic vaccines

Chem Pharm Bull (Tokyo). 1998 Nov;46(11):1676-82. doi: 10.1248/cpb.46.1676.

Authors

K Miyajima¹, T Nekado, K Ikeda, K Achiwa

Affiliation

¹ School of Pharmaceutical Sciences, University of Schizuoka, Japan.

PMID: 9845951
DOI: 10.1248/cpb.46.1676

Abstract

Conjugates (3-5) of Tn, sialyl Tn and HIV-1-derived peptide antigen with a N-tetradecanoyl L-serine-beta-alanine-containing D-glucosamine derivative, structurally related to lipid A, as an immunoadjuvant for the development of totally synthetic vaccines against cancers or HIV were synthesized. The mitogenic activity of compounds 3, 4 and 5 was stronger than that of lipid A analogs (1, 2).

MeSH terms

Adjuvants, Immunologic / chemistry*
Animals
Antigens, Tumor-Associated, Carbohydrate / chemistry*
Carbohydrate Sequence
Lipid A / analogs & derivatives*
Lipid A / chemistry*
Magnetic Resonance Spectroscopy
Mice
Mice, Inbred C3H
Molecular Sequence Data
Spectrophotometry, Infrared
Vaccines, Synthetic / chemistry*

Substances

Adjuvants, Immunologic
Antigens, Tumor-Associated, Carbohydrate
Lipid A
Tn antigen
Vaccines, Synthetic
sialosyl-Tn antigen