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Synthesis of thiourea-tethered C-glycosyl amino acids via isothiocyanate-amine coupling.

Content Provider	Semantic Scholar
Author	Barghash, Reham F. Massi, Alessandro Dondoni, Alessandro
Copyright Year	2009
Abstract	A new class of C-glycosyl amino acids displaying a thiourea segment as a linker has been designed and synthesized by addition of peracetylated glycosylmethyl isothiocyanates to an amine-functionalized amino acid (N(alpha)-Fmoc-beta-amino-l-alanine). Three pairs of compounds with alpha- and beta-galacto, alpha- and beta-gluco, and alpha- and beta-manno configuration have been prepared with yields ranging between 70 and 75%. The orthogonal set of protective groups (O-acetyl in the carbohydrate moiety and N-Fmoc in the amino acid residue) makes these compounds suitable substrates for the co-translational modification of natural peptides. The couplings of model hydroxy-free and perbenzylated glycosylmethyl isothiocyanates with the above N(alpha)-Fmoc-beta-amino-l-alanine and the N(alpha)-Boc-protected analogue have been carried out as well, thus broadening the scope of the coupling reaction. Nevertheless, there are limitations of this isothiocyanate-amine coupling in complex systems, and these are briefly discussed.
Starting Page	157
Ending Page	161
Page Count	5
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://www.rsc.org/suppdata/OB/b9/b908156a/b908156a.pdf
PubMed reference number	19641791v1
Alternate Webpage(s)	https://doi.org/10.1039/b908156a
DOI	10.1039/b908156a
Journal	Organic & biomolecular chemistry
Volume Number	7
Issue Number	16
Language	English
Access Restriction	Open
Subject Keyword	Acetylcarnitine Alanine Transaminase Amine Oxidase (Copper-Containing) Amines Amino Acid Metabolism, Inborn Errors Amino Acids Amino Acids, Branched-Chain Analog Carbohydrates Genetic Translation Process Isothiocyanate Isothiocyanates Monoamine Oxidase Post-Translational Protein Processing Thiourea beta Thalassemia hydroxyl group
Content Type	Text
Resource Type	Article

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