TY - JOUR
TI - Lanthionine chemistry. Part 5. Synthesis of cyclic non-symmetrical lanthionyl peptides
AU - Photaki, I.
AU - Caranikas, S.
AU - Samouilidis, I.
AU - Zervas, L.
JO - Journal of the Chemical Society, Perkin Transactions 1
PY - 1980
VL - null
TODO - null
SP - 1965-1970
PB - 
SN - 0300-922X, 1364-5463
TODO - 10.1039/p19800001965
TODO - null
TODO - The synthesis of a protected fragment of the antibiotic nisin, specifically Nα-benzyloxycarbonyl-D-hemilanthionyl-L- isoleucyldehydroalanyl-L-leucyl-L-hemilanthionine α′-methyl ester (B) and of its analogue Nα-benzyloxycarbonyl-L-hemilanthionyl- L-isoleucyl-L-seryl-L-leucyl-L-hemilanthionine α′-methyl ester (A) is described. For the synthesis of these unusual peptidic compounds, unsymmetrically substituted derivatives of L- or meso-lanthionine were used. For the synthesis of compound (B), the O-diphenylphosphorylserine portion of the peptide (26) was transformed by a β-elimination reaction to the dehydroalanine group in peptide (27), which after partial deprotection was subjected to cyclization. Compound (A) is a precursor of the dehydroalanine-containing cyclo-L-lanthionyl peptide. The monomeric structures of the cyclo-peptides (A) and (B) were proved by molecular-weight determination and the presence of the amino-acrylic acid grouping in the molecule of (B) was ascertained by amino-acid analysis and its i.r. spectrum.
ER -