SOLID‐PHASE PEPTIDE SYNTHESIS USING MILD BASE CLEAVAGE OF NαFLUORENYLMETHYLOXYCARBONYLAMINO ACIDS, EXEMPLIFIED BY A SYNTHESIS OF DIHYDROSOMATOSTATIN

Wiley - Tập 11 Số 3 - Trang 246-249 - 1978
Chi‐Deu Chang1, Johannes Meienhofer1
1Chemical Research Department, Hoffmann-La Roche Inc., Nutley, New Jersey, U.S.A.

Tóm tắt

N α‐9‐Fluorenylmethyloxycarbonyl (Fmoc) amino acids will be of advantage in solid phase peptide synthesis. The Fmoc‐group is quantitatively cleaved by mild base (piperidine). This permits the use of tert‐butyl‐type side chain blocking and of peptide‐to‐resin linkage cleavable by mild acidolysis. Side reactions arising from repetitive acid deprotection and final HF cleavage in contemporary solid phase synthesis are avoided. Fully bioactive and homogeneous dihydrosomatostatin was obtained in 53% overall yield.

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Tài liệu tham khảo

10.1021/ja00722a043

10.1021/jo00795a005

10.1021/ar50066a003

Chang C. D., 1978, J. Am. Chem. Soc.

10.1021/ja00792a046

10.1016/B978-0-12-516302-6.50008-6

10.1021/ja00845a034

10.1016/0003-2697(73)90040-7

Felix A. M., 1977, Peptides, 532

Felix A. M., 1978, Int. J. Pept. Prot. Res.

10.1016/S0021-9258(18)62396-8

Hagenmaier H., 1972, Hoppe-Seyler's Z. Physiol. Chem., 353, 1973

10.1016/S0076-6879(67)11031-8

10.1016/0003-2697(70)90146-6

10.1002/cber.19701030319

10.1021/ja00447a048

10.1016/0006-291X(64)90258-X

10.1021/jm00213a001

10.1016/B978-0-12-447202-0.50009-0

10.1021/ja00897a025

Merrifield R. B., 1977, Peptides, Proceedings of the Fifth American Peptide Symposium, 488

10.1016/S0040-4039(00)93112-5

J. Am. Chem. Soc., 98, 7357, 10.1021/ja00439a041

Rivier J., 1973, Compt. Rend., 276, 2737

10.1021/jm00236a001

10.1021/ja00883a059

10.1016/S0021-9258(17)33637-2

10.1002/ange.19690812313

10.1210/endo-91-2-562

Vale W., 1972, Compt. Rend. Ser. D., Paris, 275, 2913

10.1126/science.179.4068.77

Waki M., 1978, Int. J. Pept. Prot. Res.

10.1021/ja00785a602

10.1021/jo00868a025

10.1021/bi00847a034