Investigation of the synthetic route to pepstatin analogues by SPPS using O-protected and O-unprotected statine as building blocks.
The synthetic route to pepstatin derivatives by a solid phase peptide synthesis using either O-protected or O-unprotected statine as a building block has been investigated. Statine was prepared according to a modified literature procedure, whereas protection of its 3-hydroxyl moiety using tert-butyldimethylsilylchloride (TBSCl) provided the novel O-TBS-protected statine building block. The O-tert-butyldimethylsilyl (TBS)-protected statine approach provides an improved synthetic strategy for the preparation of statine-containing peptides as demonstrated by the synthesis of the pepstatin analogue iva-Val-Leu-Sta-Ala-Sta.
Cadicamo
Cosimo D
CD
Department of Organic Chemistry, FU Berlin, Takustrasse 3, D-14195 Berlin, Germany.
Asante
Vivian
V
Abu Ammar
Morhaf
M
Borelli
Claudia
C
Korting
Hans C
HC
Koksch
Beate
B
D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005449:Fluorenes / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010436:Pepstatins / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D005449:Fluorenes; D007202:Indicators and Reagents; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D010436:Pepstatins; C031375:pepstatin; C013165:statine