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Synthesis of Highly Functionalized Amino Acids: An Expedient Access to L ‐ and D ‐β‐Hydroxyenduracididine Derivatives
Author(s) -
Schwörer Clemens J.,
Oberthür Markus
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900971
Subject(s) - chemistry , guanidine , stereocenter , amino acid , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , enantioselective synthesis , biochemistry
Abstract The nonproteinogenic amino acids (3 S ,4 S )‐ L ‐ and (3 S ,4 S )‐ D ‐β‐hydroxyenduracididine (βhEnd), each containing a cyclic guanidine group and three contiguous stereocenters, have been synthesized for the first time, starting from commercially available diacetone D ‐glucose. The key inversion reactions for the introduction of the two nitrogen groups at C‐2 and C‐4 afford products that are diastereomerically pure and easy to purify, thereby allowing the gram‐scale preparation of βhEnd derivatives that are suitably protected for peptide coupling reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)