- An Atom-Economic Inverse Solid-Phase Peptide Synthesis Using Bn or BcM Esters of Amino Acids
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An atom-economic N-to-C-directed solid-phase peptide synthesis is reported that uses benzyl (Bn) or (benzhydryl-carbamoyl)-methyl (BcM) esters of amino acids as the building blocks, which facilitate efficient hydrazinolysis, convenient conversion to acyl azide, and robust amidation with the next amino acid ester. This method is free of coupling reagents and free of protection on the side-chain OH, CO2H, CONH2, etc., therefore exhibiting a significantly improved atom economy compared to those of BOC- or Fmoc-based C-to-N-directed approaches.
- Huang, Wei,Li, Jian,Liu, Bo,Tang, Feng,Zheng, Xing,Zhu, Yue
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supporting information
p. 7571 - 7574
(2021/10/02)
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- In Vitro Assessment of Putative PD-1/PD-L1 Inhibitors: Suggestions of an Alternative Mode of Action
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The programmed cell death protein 1 (PD-1) signaling axis is among the most important therapeutic targets in modern oncology. Aurigene Discovery Technologies Ltd. (Aurigene) has patented a series of peptidomimetic small molecules derived from the PD-1 pro
- Blevins, Derek J.,Hanley, Ronan,Bolduc, Trevor,Powell, David A.,Gignac, Michael,Walker, Kayleigh,Carr, Mark D.,Hof, Fraser,Wulff, Jeremy E.
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supporting information
p. 1187 - 1192
(2019/08/27)
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- PEPTIDOMIMETIC COMPOUNDS AS IMMUNOMODULATORS
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The present invention relates to novel peptidomimetic compounds as therapeutic agents capable of inhibiting the programmed cell death 1 (PD1) signalling pathway. The invention also relates to derivatives of the therapeutic agents. The invention also encom
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Paragraph 0193; 0194
(2013/09/26)
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- Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO
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α-Aminoesters react with Ph3PCCO in a domino addition-Wittig cyclization sequence affording enantiomerically pure tetramates. In the case of β-oxo functionalized α-aminoesters, e.g., esters of serine, threonine or β-hydroxyornithine the yields of this reaction depend heavily on the bulkiness of the β-OR group and on the configuration of β-carbon atom C-3. Smaller residues and 2R/3R-configured aminoesters give better yields. The alkoxycarbonyl group of the ester moiety and the residue on the N-atom are less important. These findings can be accounted for by assuming an early puckered transition state for the intramolecular ring-closing Wittig reaction. The addition of sub-stoichiometric amounts of benzoic acid or N-hydroxysuccinimide (for acid-sensitive compounds) is advantageous in some cases as it accelerates the formation of the intermediate amide ylides.
- Loke, Inga,Park, Natja,Kempf, Karl,Jagusch, Carsten,Schobert, Rainer,Laschat, Sabine
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supporting information; experimental part
p. 697 - 704
(2012/01/05)
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- Spirodiepoxides in total synthesis: Epoxomicin
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The first use of the spirodiepoxide functional group in total synthesis, a study culminating in an efficient synthesis of the potent proteasome inhibitor epoxomicin, is described. Spirodiepoxides derived from allenes by oxidation are shown to give syn dis
- Katukojvala, Sreenivas,Barlett, Kristin N.,Lotesta, Stephen D.,Williams, Lawrence J.
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p. 15348 - 15349
(2007/10/03)
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- Synthesis of O-Glycopeptides of the N-Terminus of Interleukin-2
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The synthesis of a number of O-glycopeptides with different lengths of chain of between 3 and 10 amino acids that are part of the N-terminus of interleukin-2 is described.The key intermediate for the syntheses is O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-(9-fluorenylmethoxycarbonyl)-L-threonine tert-butyl ester (9b), to which suitably protected amino acids and peptides can be added C- or N-terminally. 9b is an element, which allows to insert glycosylated hydroxyamino acids with the Fmoc/tBu combination of protective groups, which are approved in peptide synthesis.During the syntheses peptide blocks are used.With the deprotected products it is possible to test the structural specificity of glycosyl transferases.
- Paulsen, Hans,Adermann, Knut
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p. 751 - 770
(2007/10/02)
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