A Short Synthesis of Partially Protected L- and D-beta-Hydroxyenduracididines and a Structurally Simplified Dipeptide Analogue

A short synthesis of the C2-epimeric amino acids L-and D-beta-hydroxyenduracididine(beta hEnd) was developed. Both amino acids are part of the cyclopeptide portion of the mannopeptimycin antibiotics. The synthetic route comprises eight steps starting from Garner's aldehyde and provides partiall...

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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 46; no. 16; pp. 2234 - 2240
Main Authors Fischer, Sebastian N., Schwoerer, Clemens J., Oberthuer, Markus
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
natural products
STREPTOMYCES-HYGROSCOPICUS
cyclic guanidine
peptide coupling
amino acids
stereoselective synthesis
ANTIBACTERIAL
GLYCOPEPTIDES
LL-AC98
MANNOPEPTIMYCINS
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Summary:A short synthesis of the C2-epimeric amino acids L-and D-beta-hydroxyenduracididine(beta hEnd) was developed. Both amino acids are part of the cyclopeptide portion of the mannopeptimycin antibiotics. The synthetic route comprises eight steps starting from Garner's aldehyde and provides partially protected derivatives in good overall yields. Key steps are a stereodivergent olefination-bishydroxylation sequence and a regioselective guanidine cyclization reaction. In addition, precursor amino acids that contain a protected amino alcohol instead of the cyclic guanidine could be efficiently coupled to provide a structurally simplified analogue of the L-beta hEnd-D-beta hEnd dipeptide portion of the mannopeptimycin aglycone.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0033-1341236