88597-05-1Relevant articles and documents
Design and Synthesis of Macromonocyclic Polyamines Composed of Natural Methylene Arrays
Iwata, Masaaki,Kuzuhara, Hiroyoshi
, p. 198 - 210 (2007/10/02)
A general synthetic method applicable to acyclic and cyclic polyamines was developed.The methodology was exemplified by systematical synthesis of twelve macromonocyclic polyamines, 1 (N4) through 12 (N8), composed of the combination of four natural polyamine segments, spermidine, spermine, thermine, and thermospermine.These twelve designed macrocycles are exhausted numbers of possible structures defined by three arbitrarily chosen criteria concerning with methylene chain arrays and nitrogen content (four to eight).The common elements of the structural characteristics were analyzed and were found to be reduced to readily available three classes of simple N,N'-ditosylalkanediamines derived from diamines and triamine.Nitrogen content was increased systematically through the reaction of N,N'-ditosylalkanediamine with one of three ω-phthalimidated electrophiles followed by regeneration of the same functionality at symmetrical both terminals as the starting materials via a series of transformation reaction, in excellent yields.Tractable formamide intermediate profits the facile synthesis of acyclic polyamines with long chains.Cyclization was achieved, under high dilution conditions, through the reaction of α,ω-bis(tosylamide) with α,ω-ditosylates in DMF in the presence of cesium carbonate.The cyclization occurred in practical synthetic yields even in the formation of multi-membered ring when the shorter electrophile and the longest α,ω-bis(tosylamide) reacted.
The biosynthesis of the streptolidine moiety in streptothricin F
Martinkus,Tann,Gould
, p. 3493 - 3505 (2007/10/02)
A series of arginines specifically labeled either with 13C and 15N or with 2H were synthesized and fed to Streptomyces L-1689-23. The streptothricin F isolated in each case was analyzed by either 13C or 2H NMR, respectively, in order to determine the labeling pattern obtained. From these results, it appears that arginine is metabolized to a β-ketoarginine, possibly via a pyridoxal phosphate adduct, and then via cyclization, reduction, rearrangement, and hydroxylation to the streptolidine moiety. The pathway described can also account for the formation of other known antibiotics, and for β-hydroxy-γ-amino acids, generally.
