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Conformationally restricted diamines and amino alcohols

The primary structure of a peptide can be formally considered as a oligoethylenediamine molecular platform to which the side chains and carbonyl oxygen atoms are attached through single and double bonds respectively. This backbone is conformationally restrained at the amide bonds and has some rotational degrees of freedom at single C-C and C-N bonds. The later become restricted upon the formation of the secondary structures stabilized by multiple hydrogen bonds. The fragments of 1,3-, 1,4-, 1,5- and 1,6-diamines are found in peptides containing aspargine, glutamine, tryptophane, histidine, lysine and arginine. Apparently some structural, conformational and functional features of peptides can be reproduced by designed derivatives of synthetic conformationally restrained diamines.

Diamine units in peptides.

Recently, Enamine has initiated an in-house project focusing on multigram scale syntheses of known and novel conformationally restricted monoprotected diamines and amino alcohols which can be used as molecular scaffolds in rational design of drugs and peptidomimetics bearing two different functional groups in well defined spatial arrangements.

Our minilibrary of monoprotected conformationally restricted cyclic diamines comprises molecules containing 1,2- or 1,3-diamine units adopting anti- configuration. The arrangement of amino groups in these diamines is similar to that in peptide chains of the -sheet secondary structures. High level of preorganization and low conformational mobility are distinguishing characteristics of many bicyclic compounds containing units of 1,2-, 1,3- and 1,4-diamines. The arrangement of amino groups in some molecules is virtually constrained whereas structures of other proposed diamines allow certain rotational degrees of freedom.

A set of conformationally constrained diamine building blocks is proposed either from stock or for re-synthesis.

Monocyclic diamines

EN300-39611 EN300-36333 EN300-27334
EN300-51971 EN400-13487 EN300-36785
EN300-09148 EN300-18293 EN300-31523
EN300-24147 EN400-13488 EN400-15766

Bicyclo[m.n.0]alkane diamines

EN300-36998 EN400-13232 EN400-12787
EN400-12786 EN400-15263 EN400-15264
EN400-15270 EN400-13916 EN400-15594
EN400-13072 EN400-13926 EN400-13928
EN300-51015 EN400-13953 EN300-26877
EN300-36885 EN300-27689 EN400-13047
EN400-15244 EN400-15245

Other Bicyclo[m.n.k]alkane diamines

EN300-40961 EN300-43280 EN400-13980
EN400-13907 EN300-42408 EN400-15275
EN400-15274 EN400-12788 EN300-27793

Spiroalkane diamines

EN300-26948 EN300-27604 EN400-13042
EN400-15843 EN400-15604

Other diamines

EN300-29501 EN300-29690 EN300-29969
EN400-13362 EN400-13364 EN400-13365

Conformationally restricted amino alcohols. All products are >96% chemically pure,
and >95% (mostly > 99%) optically pure.

IDStructureChemical name
EN400-13917 (1S,5S)-2-azabicyclo[3.1.0]hex-1-ylmethanol
EN400-13918 (1R,3S,4S)-2-azabicyclo[2.2.1]hept-3-ylmethanol
EN400-13919 (1R,3S,4S)-[2-((1R)1-phenylethyl)-2-
EN400-13073 tert-butyl 3-hydroxycyclobutylcarbamate
EN400-13920 tert-butyl 6-hydroxyspiro[3.3]hept-2-ylcarbamate



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