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Heterospirocyclic N ‐(2 H ‐Azirin‐3‐yl)‐ L ‐prolinates: New Dipeptide Synthons
Author(s) -
Suter Giovanni,
Stoykova Svetlana A.,
Linden Anthony,
Heimgartner Heinz
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20001108)83:11<2961::aid-hlca2961>3.0.co;2-s
Subject(s) - chemistry , synthon , dipeptide , stereochemistry , combinatorial chemistry , biochemistry , amino acid
The synthesis of methyl N ‐(1‐aza‐6‐oxaspiro[2.5]oct‐1‐en‐2‐yl)‐ L ‐prolinate ( 1e ) has been performed by consecutive treatment of methyl N ‐[(tetrahydro‐2 H ‐pyran‐4‐yl)thiocarbonyl]‐ L ‐prolinate ( 5 ) with COCl 2 , 1,4‐diazabicyclo[2.2.2]octane (DABCO), and NaN 3 ( Scheme 1 ). As the first example of a novel class of dipeptide synthons, 1e has been shown to undergo the expected reactions with carboxylic acids and thioacids ( Scheme 2 ). The successful preparation of the nonapeptide 16 , which is an analogue of the C‐terminal nonapeptide of the antibiotic Trichovirin I 1B , proved that 1e can be used in peptide synthesis as a dipeptide building block ( Scheme 3 ). The structure of 7 has been established by X‐ray crystal‐structure analysis ( Figs. 1 and 2 ).