TY - JOUR
T1 - Structure and Chemical Properties of Ptilomycalin A
AU - Ohtani, Ikuko
AU - Kusumi, Takenori
AU - Kakisawa, Hiroshi
AU - Kashman, Yoel
AU - Hirsh, Shulamit
PY - 1992/10/1
Y1 - 1992/10/1
N2 - The structure of ptilomycalin A (1), a marine alkaloid possessing potent antiviral and antibiotic activites, has been determined on the basis of NMR analyses of its trifluoroacetyl (TFA) derivative (2). It has a unique structure consisting of a polycyclic guanidine and a spermidine group, each of which is linked to a 16-hydroxyhexadecanoic acid moiety. The rotational isomerism of the acylated sperimidine moiety of 2 has been studied by comparing the NMR properties of the synthetic trifluoroacetyl derivatives of spermidine (5), dipropylenetriamine (11), diethylenetriamine (12), and pentylamine (13). From these experiments, a plausible conformation of 2 and ptilomycalin A (1) has been proposed as shown in 2c, in which an anion is trapped between the guanidine and spermidine moieties. The TFA derivative 2 acts as a phase-transfer agent. NMR analysis of the stability of the complexes formed between 2 and several organic carboxylates in CDCl3 solutions has been carried out.
AB - The structure of ptilomycalin A (1), a marine alkaloid possessing potent antiviral and antibiotic activites, has been determined on the basis of NMR analyses of its trifluoroacetyl (TFA) derivative (2). It has a unique structure consisting of a polycyclic guanidine and a spermidine group, each of which is linked to a 16-hydroxyhexadecanoic acid moiety. The rotational isomerism of the acylated sperimidine moiety of 2 has been studied by comparing the NMR properties of the synthetic trifluoroacetyl derivatives of spermidine (5), dipropylenetriamine (11), diethylenetriamine (12), and pentylamine (13). From these experiments, a plausible conformation of 2 and ptilomycalin A (1) has been proposed as shown in 2c, in which an anion is trapped between the guanidine and spermidine moieties. The TFA derivative 2 acts as a phase-transfer agent. NMR analysis of the stability of the complexes formed between 2 and several organic carboxylates in CDCl3 solutions has been carried out.
UR - http://www.scopus.com/inward/record.url?scp=0026443070&partnerID=8YFLogxK
U2 - 10.1021/ja00048a018
DO - 10.1021/ja00048a018
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AN - SCOPUS:0026443070
SN - 0002-7863
VL - 114
SP - 8472
EP - 8479
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 22
ER -