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Synthesis of polyamine‐carbodiimides. — Potential activators for chemical ligations of oligodeoxynucleotide 3′‐phosphates
Author(s) -
von Kiedrowski Günter,
Dörwald Florencio Zaragoza
Publication year - 1988
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198819880814
Subject(s) - chemistry , polyamine , alkyl , spermine , yield (engineering) , formamide , derivative (finance) , nucleophile , polyamine oxidase , chemical synthesis , combinatorial chemistry , organic chemistry , biochemistry , catalysis , in vitro , enzyme , economics , financial economics , materials science , metallurgy
Polyamine‐Carbodiimides are new water‐soluble activating agents designed to fit some requirements of chemical ligations of oligodeoxynucleotide 3′‐phosphates. N ‐Alkyl‐ N ′‐(4,9,13‐trimethyl‐4,9,13‐triazatetradecyl)carbodiimides 9 have been prepared from 4,9,13‐trimethyl‐4,9,13‐triazatetradecylamine ( 2b ), a N ‐methylated derivative of spermine ( 2a ), via the respective thioureas 8 . An efficient total synthesis of the polyamine 2b has been elaborated in which the carbon‐nitrogen framework of 2b is assembled through succesive N ‐alkylations of tosylamides as the key steps starting from N ‐[4‐(tosylamido)butyl]formamide ( 4d ), N ‐(3‐iodopropyl)‐ N ‐methyl‐ p ‐toluenesulfonamide ( 3c ), and 1‐bromo‐3‐chloropropane ( 3a ). The polyamine 2b could be obtained via seven steps ( 3c + 4d → 5a , 5a → 5b , 5b → 5c , 5c + 3a → 6b , 6b → 6d , 6d → 6f , 6f → [ 6g ] → 2b ) in 40% overall yield.