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Direct Fmoc/ tert ‐Bu solid phase synthesis of octamannosyl polylysine dendrimer–peptide conjugates
Author(s) -
Kantchev Eric Assen B.,
Chang ChungChieh,
Chang DingKwo
Publication year - 2005
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.20403
Subject(s) - chemistry , dendrimer , conjugate , polylysine , peptide , peptide synthesis , combinatorial chemistry , solid phase synthesis , phase (matter) , stereochemistry , organic chemistry , biochemistry , mathematical analysis , mathematics
The mannose binding proteins on the surface of the dendritic cells are responsible for capture of pathogens in the early stages of immune response. Conjugation to mannose dendrimers is a rarely explored but potentially powerful strategy for enhancing immunogenicity of synthetic peptides relying on direct delivery to dendritic cells. We describe a general protocol for preparation of pure, monodisperse third‐generation mannosylated poly‐ L ‐lysine dendrimer‐peptide conjugates using direct, machine‐assisted Fmoc/ t ‐Bu solid phase peptide synthesis. The glycodendrons were elaborated onto the N‐ or C‐terminus of sequences derived from HIV‐1 gp41, SARS‐CoV S2 protein, and Influenza Hemagglutinin (consisting of 15–44 residues). The products were obtained in a homogeneous state after cleavage from the resin, deprotection, and a single purification on semipreparative RP–HPLC. © 2005 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 84: 232–240, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com