Protease-Catalyzed Peptide Synthesis from N- to C-Terminus: An Advantageous Strategy

✍ Scribed by Frank Bordusa; Dr. Dirk Ullmann; Prof. Dr. Hans-Dieter Jakubke

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 442 KB
• Volume: 36
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.199710991

✦ Synopsis

Compounds 7a--7c and 8-10 all gave a single major peak by reversed-phase HPLC (>SO% purity). Retention factors [(elution time)/(solvent front)] were 4.69, 7.20, 7 90. 3.77. 7.12, and 7.79, respectively (4.5 x 250 mm octadecasiliyl column, solvent A = 0.1 % TFA In water, solvent B = 0.1 % TFA in acetonitrile, gradient elution of 100% A to 100% B over 40 minutes. monitored at 220nni). ESMS information was entirely consistent with the formation of the expected compounds: miz (%), 7a 324.2( 100)[MHt], 7b4374(100) [MH'], 7c 494.3(100) [MH'], 8 394.3(100) [MH-1; 9 526.3(100) 303 -310 Scheme 2. Coupling two differently labile linkers to the resin prior to library synthesis and inversion, to afford an Edman-sequencable coding strand attached to the resin after peptide cleavage. a) 1 % TFAICH,CI2; b) MeOH, c) 100% TFA.

halomethyl and acyloxymethyl ketones at the C-termini of peptides. This technique thus offers "another end to peptide synthesis".