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- W2055803280 abstract "A block synthesis of the model compound for the phytoalexin elicitor-active glycoprotein is described. Combination of the C-terminus free compounds, N-(9-fluorenylmethoxycarbonyl)-O-(tert-butyl)-L-seryl-L-proline (1) or N-(9-fluorenylmethoxycarbonyl)-(2,3,4,6-tetra-O-acetyl-beta-D-g luc opyranosyl) -(1-->6)-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->6) -(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-L-seryl-L-proline (2) with the N-terminus free compounds, 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl -(1-->6)-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->6)-(2,3,4-tri- O -acetyl-alpha-D-mannopyranosyl)-L-seryl-L-prolyl-L-seryl-L-proline methyl ester (4), O-(tert-butyl)-L-seryl-L-prolyl-(2,3,4,6-tetra-O-acetyl-beta-D -glucopyranosyl)-(1-->6)-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl) -(1-->6)-(2,3,4-tri-O-acetyl- alpha-D-mannopyranosyl)-L-seryl-L-proline methyl ester (6) or 2,3,4,6-tetra-O-acetyl-beta-D- glucopyranosyl -(1-->6)-(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->6) -(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-L-seryl-L-prolyl -(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-(1-->6) -(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-(1-->6) -(2,3,4-tri-O-acetyl-alpha-D-mannopyranosyl)-L-seryl-L-proline methyl ester (8), by use of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ) gave three hexaglycosyl hexapeptides and a nonaglycosyl hexapeptide derivatives (9, 11, 14, and 17). These N-terminus free compounds were derived from triglycosyl tetrapeptides (3 and 5) or a hexaglycosyl tetrapeptide (7) on selective deblock reaction by morpholine. The hexaglycosyl hexapeptides (10, 13, and 16) and the nonaglycosyl hexapeptide (18) have been prepared by the convergent block synthesis." @default.
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- W2055803280 date "1996-11-01" @default.
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- W2055803280 title "Synthesis of glycopeptides with phytoalexin elicitor activity — III. Syntheses of hexaglycosyl hexapeptides and a nonaglycosyl hexapeptide" @default.
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- W2055803280 doi "https://doi.org/10.1016/s0968-0896(96)00170-8" @default.
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