ISSN:
1573-3904
Keywords:
peptidep-aminoanilides
;
peptidep-nitroanilides
;
SasrinTM
;
sodium perborate as oxidant
;
SPPS
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary Peptidep-nitroanilides (peptidepNAs) have found wide application as chromogenic substrates. An improved SPPS method to synthesize rapidly and in good yield a broad range of peptidepNAs under mild conditions will be presented here. To obtain a suitable carrier, the (4-aminophenyl)aminocarbonyloxy derivatives of Wang resin and Sasrin were synthesized. SPPS employing Fmoc/tBu-based protection followed by acidolytic cleavage yielded the (protected) peptidep-aminoanilide which was oxidized with sodium perborate in acetic acid to yield the (protected) peptidepNA. Side-chain protection proved to be advantageous. Acid-labile peptidepNAs such as the proteasome substrate Z-Glu(OtBu)-Ala-Leu-pNA thus can be obtained directly. The behavior of Cys, Met, Tyr and Trp being susceptible towards oxidation was studied more closely.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF02443555
