Synthetic studies towards peptidyl nucleoside antibiotics: first synthesis of a polyoxamic acid derivative enabling direct coupling with α-amino acid esters

1997 ◽  
pp. 691-692 ◽  
Author(s):  
Claudio Palomo ◽  
Mikel Oiarbide ◽  
Aitor Esnal
Keyword(s):  
Amino Acid ◽  
Acid Derivative ◽  
Direct Coupling ◽  
Amino Acid Esters ◽  
Nucleoside Antibiotics ◽  
Synthetic Studies ◽  
Acid Esters

Versatility of β-lactams in synthesis. Studies directed toward the synthesis of complex nucleoside antibiotics and some macrocyclic peptides

2000 ◽  
Vol 72 (9) ◽  
pp. 1763-1768 ◽  
Author(s):  
Claudio Palomo ◽  
Jesús M. Aizpurua ◽  
Iñaki Ganboa ◽  
Mikel Oiarbide
Keyword(s):  
Amino Acid ◽  
Ring Expansion ◽  
Amino Acid Esters ◽  
Short Route ◽  
Nucleoside Antibiotics ◽  
Macrocyclic Peptides ◽  
Acid Esters

The diastereoselective [2+2] cycloaddition of α-hydroxyketene equivalents with chiral α,ω-oxyaldehyde-derived imines followed by the 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO)-promoted ring expansion of the resulting α-hydroxy β-lactam adducts provides an unconventional and short route to α-amino acid N-carboxy anhydrides (NCAs). The required enantiopure α,ω-oxyaldehydes were obtained either from the chiral pool or through the Sharpless AD methodology. Following the present strategy, several nonproteinogenic NCAs were synthesized, which were further coupled with α-amino acid esters giving rise to key fragments of some nucleoside antibiotics and macrocyclic peptides.

Synthesis of (S)- and (R)- tert Leucine Enabling Direct Coupling with α-Amino Acid Esters via β-Lactam-Derived α-Amino Acid N-Carboxy Anhydrides.

1997 ◽  
Vol 38 (17) ◽  
pp. 3093-3096 ◽  
Author(s):  
Claudio Palomo* ◽  
Iñaki Ganboa ◽  
Beatriz Odriozola ◽  
Anthony Linden
Keyword(s):  
Amino Acid ◽  
Direct Coupling ◽  
Amino Acid Esters ◽  
Acid Esters

Asymmetric Preparation of anti-β-Hydroxyα-amino Acid Esters

Synfacts ◽  
2006 ◽  
Vol 2006 (12) ◽  
pp. 1253-1253
Author(s):  
Y. Hamada ◽  
K. Makino ◽  
M. Iwasaki
Keyword(s):  
Amino Acid ◽  
Amino Acid Esters ◽  
Acid Esters

Antiviral activity of glycyrrhizic acid conjugates with amino acid esters against Zika virus

2021 ◽  
Vol 294 ◽  
pp. 198290
Author(s):  
Lidia A. Baltina ◽  
Mann-Jen Hour ◽  
Ya-Chi Liu ◽  
Young-Sheng Chang ◽  
Su-Hua Huang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Antiviral Activity ◽  
Zika Virus ◽  
Glycyrrhizic Acid ◽  
Amino Acid Esters ◽  
Acid Esters
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