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PREPARATION AND PROPERTIES OF Nα-9-FLUORENYLMETHYLOXYCARBONYLAMINO ACIDS BEARING TERT.-BUTYL SIDE CHAIN PROTECTION
Authors:CHI-DEU CHANG  MICHINORI WAKI  MUSHTAQ AHMAD  JOHANNES MEIENHOFER  EDWIN O. LUNDELL  JAMES D. HAUG
Abstract:The preparation is described of several Nα-9-fluorenylmethyloxycarbonylamino acids and derivatives bearing tert.-butyl type side-chain protection of amine, carboxyl, guanido, hydroxyl, imidazol, and sulfhydryl functionalities. Physicochemical properties of these compounds have been determined. Cleavage of the Fmoc group by various amines appears to depend on the base strength and steric hindrance. Premature deblocking of Fmoc group by amine on solid support is very slow and may be negligible under the conditions of solid-phase synthesis.
Keywords:optical rotation    -fluorenylmethyloxycarbonylamino acids  Fmoc cleavage by different bases  stability in solid phase synthesis
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