Abstract:
:A new strategy for designing synthetic vaccines is presented. In this approach synthetic peptides are conformationally restricted by replacing putative hydrogen bonds with covalent mimics. The chemistry for substituting a hydrazone-ethane link (N-N = CH-CH2-CH2) for an (i + 4)----i hydrogen bond in a pentapeptide with alpha-helical potential is reported. Chemically shaping peptides to mimic the three-dimensional surfaces of proteins may enhance their immunogenicity. To test this strategy, a potential synthetic vaccine for malaria, Cys-(Asn-Pro-Asn-Ala)3-NH2, was conformationally restricted by replacing putative hydrogen bonds between asparagine side chains with a covalent replacement, an ethylene bridge, to give first generation chemically shaped immunogens. Antibodies to one of the shaped malarial peptides show a strong reaction with living Plasmodium falciparum sporozoites, a form of malaria which infects hundreds of millions of people yearly.
journal_name
Vaccinejournal_title
Vaccineauthors
Satterthwait AC,Arrhenius T,Hagopian RA,Zavala F,Nussenzweig V,Lerner RAdoi
10.1016/s0264-410x(88)80007-0subject
Has Abstractpub_date
1988-04-01 00:00:00pages
99-103issue
2eissn
0264-410Xissn
1873-2518pii
S0264-410X(88)80007-0journal_volume
6pub_type
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