Rapid and efficient preparative purification of building blocks suitable for solid-phase synthesis of neoglycopeptides: Synthesis and purification ofO-(2,3,4,6-tetra-O-acetyl-β-d- galactopyranosyl/glucopyranosyl)-Nα-fluoren-9-yl- methoxycarbonyl-hydroxyproline

✍ Scribed by Josep Lluís Torres; Eugènia Pagans; Pere Clapés

• Book ID: 104632111
• Publisher: Springer Netherlands
• Year: 1996
• Tongue: English
• Weight: 504 KB
• Volume: 3
• Category: Article
• ISSN: 1573-3149
• DOI: 10.1007/bf00126734

✦ Synopsis

As part of scaling-up studies for the preparation of antinociceptive neoglycopeptides, the purification of appropriate glycosylated building blocks has been optimized. The synthesis and purification of O-(2,3,4,6-tetra-O-acetyl-13-D-ga~act~pyran~sy~g~uc~pyran~sy~)-N%flu~ren-9-y~-meth~xycarb~ny~-hydr~xypr~ine is described in this paper. The building blocks, suitable for solid-phase synthesis, are obtained in a single chemical step from partially protected hydroxyproline, followed by a rapid and efficient preparative purification. Preparative reversed-phase HPLC conditions have been adjusted to maximize recoveries, while reducing both time and costs of consumables. For the galactosyl conjugate, up to 0.5 g of pure !yophilized building block was obtained from 1.5 g of a crude reaction mixture using plain deionized water and less than 2 1 of preparative-grade CH3CN. The glucosyl derivative was even more efficiently purified by spontaneous after-column crystallization from the elution mixture.