Abstract
The synthesis of N-protected glycosyl amino acids from amines has been investigated and it was found that, under microwave conditions, glycosylamines could be hydrolyzed leading to new products containing a glycosyl ester linkage. The efficiency of the microwave-induced glycosylation of aspartic acid was studied comparing the microwave activity between amide and ester bond formation. Different sugar moieties have been employed to demonstrate the simple and reproducible coupling methodology. New glycosyl ester compounds were further characterized by NMR spectroscopy.
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Abbreviations
- DCM:
-
Dichloromethane
- FCC:
-
Flash column chromatography
- Fmoc:
-
9H-Fluoren-9-ylmethoxycarbonyl
- H2BC:
-
Heteronuclear two bond correlation
- HMBC:
-
Heteronuclear multiple bond correlation
- HSQC:
-
Heteronuclear single quantum coherence
- MS:
-
Mass spectrometry
- MW:
-
Microwave
- NMM:
-
N-Methylmorpholine
- NMR:
-
Nuclear magnetic resonance
- RP-HPLC:
-
Reverse phase-high performance liquid chromatography
- SPGPS:
-
Solid phase glycopeptide synthesis
- TBCR:
-
Triazine-based coupling reagent
- t-Bu:
-
tert-Butyl
- TFA:
-
Trifluoroacetic acid
- TLC:
-
Thin layer chromatography
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Acknowledgments
We acknowledge Ente Cassa Risparmio di Firenze for supporting PeptLab. We thank Dr. Duccio Lambardi for his contribution in performing the high resolution mass spectra.
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Real-Fernández, F., Nuti, F., Bonache, M.A. et al. Microwave-assisted reaction of glycosylamine with aspartic acid. Amino Acids 39, 599–604 (2010). https://doi.org/10.1007/s00726-010-0484-8
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DOI: https://doi.org/10.1007/s00726-010-0484-8