ISSN:
1573-3904
Keywords:
SRIF
;
Somatostatin
;
Lanthionine
;
Kaiser-oxime resin
;
Peptide cyclization
;
PCOR
;
Solid-phase peptide synthesis
;
Fmoc cleavage with DBU
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary The synthesis of the lanthionine analog of somatostatin[1–14] on a Kaiser-oxime resin is described. The 12-residue peptide segment [3–14] was assembled and cyclized on the resin by using the method of peptide cyclization on an oxime resin (PCOR); the product was obtained with good yield (41%) and purity (94%). The Fmoc protecting group on the N-terminus was cleaved with DBU, followed by a 2+12 segment condensation in solution. The chromatographic (HPLC, CZE) and spectral (UV, NMR) properties of the lanthionine and the natural somatostatins have been studied and compared. Preliminary biological tests show that the lanthionine and the natural somatostatins exhibit similar binding affinities to somatostatin receptor SSTR2.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00126277
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