- Presentation and detection of azide functionality in bacterial cell surface proteins
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An improved protocol for copper-catalyzed triazole formation on the bacterial cell surface is described. Addition of highly pure CuBr to cells treated with azidohomoalanine (2) leads to ca. 10-fold more extensive cell surface labeling than previously observed. This highly active catalyst allows detection of the methionine analogues azidoalanine (1), azidonorvaline (3), and azidonorleucine (4) in cell surface proteins. Azidoalanine was previously believed to be silent with regard to the cellular protein synthesis machinery.
- Link, A. James,Vink, Mandy K. S.,Tirrell, David A.
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- Diaminodiacid-based synthesis of macrocyclic peptides using 1,2,3-triazole bridges as disulfide bond mimetics
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A new approach for the efficient construction of 1,2,3-triazole bridges as disulfide surrogates in peptides, utilizing the diaminodiacid strategy was established. Two thanatin derivatives were prepared with 1,5- and 1,4-disubstituted 1,2,3-triazole diaminodiacids as building blocks. The antibacterial activity studies are also described here.
- Guo, Ye,Liu, Chao,Song, Hui,Wang, Feng-Liang,Zou, Yan,Wu, Qiu-Ye,Hu, Hong-Gang
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p. 2110 - 2114
(2017/01/21)
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- A concise route to L-azidoamino acids: L-azidoalanine, L-azidohomo-alanine and L-azidonorvaline
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A simple and highly efficient synthetic route to three homologous azidoamino acids, starting from inexpensive, commercially available, protected natural amino acids is reported. The products can be used to introduce bioorthogonal handles into proteins. Ge
- Roth, Stefanie,Thomas, Neil R.
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scheme or table
p. 607 - 609
(2010/09/18)
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- Syntheses of optically pure α-amino acids from 3-amino-2-oxetanone salts
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A process for the preparation of optically pure α-amino acids comprising the nucleophilic ring-opening of 3-amino-2-oxetanone salts. N-Protected serine β-lactones are deprotected to form heretofore unknown 3-amino-2-oxetanone and its corresponding salts. In turn these previously unknown 3-amino-2-oxetanone salts may be used in the synthesis of other novel or rare stereochemically-pure free amino acids.
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