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Fmoc-Asp-Cys(Acm)-His-Leu-Gln-Ala-Val-Val-Leu-His-Leu-Ala-Arg-Arg-Ser-Val-Cys(Acm)-Val-His-Pro-Gln-Asn-Arg-Ser-Leu-Ala-Arg-Trp-Leu-Glu-Arg-Gln-Gly-S-CH2CH2CO-Leu-NH2[ No CAS ]
General procedure: All protected amino acids were coupled in CH2Cl2 (5 ml) using DCC (2.5 equiv.) and HOBt (2.5 equiv.) until completion (3 h) judged by Kaiser [15] ninhydrin test. After coupling of the appropriate amino acid, Boc deprotection was effected by use of TFA/CH2Cl2 (1:1, 5 ml)) for 5 min first then repeated for 25 min. Following neutralization with 10% TEA/CH2Cl2 three times (5-5 ml of each), the synthetic cycle was repeated to assemble the resin-bond protected peptide. The peptides were cleaved from the resin with simultaneous side chain deprotection by acidolysis with anhydrous hydrogen fluoride (5 ml) containing 2% anisole, 8% dimethyl sulfide and indole at 5 C for 45 min. The crude peptides were dissolved in aqueous acetic acid and lyophilized.
General procedure: The title compounds were prepared in a parallel fashion by thefollowing protocol: Step 1: To a 0.325M solution of amino acid in DMF (400 muL, 125 mumol, 1 eq) was added a 0.325M solution of 4-tert-butyl-1,2-diaminobenzene in DMF (400 muL, 125 mumol, 1 eq), a 0.325M solutionof HATU in DMF (400 muL, 125 mumol, 1 eq) and triethylamine(35 muL, 250 5 mumol, 2 eq). The reaction was shaken at 60 °C for 16 hbefore concentrating in vacuo. To the residue was added HOAc(1.25 mL) and the reaction shaken at 80 °C for 3 h. The reaction wascooled, concentrated in vacuo and purified using preparative HPLC toafford the benzimidazole intermediate. Step 2: To the benzimidazolewas added a solution of TFA/DCM (1:5, 2 mL) and the reaction wasshaken at 30 °C for 1 h. The reaction was concentrated in vacuo to affordthe final compounds as their TFA salts. LCMS QC: Column: Welch XBC182.1x50mm 5 pm, 50 °C, mobile phase A: 0.0375percent TFA in water;mobile phase B: 0.01875percent TFA in acetonitrile. Initial gradient 15 1percent B;0.60 mins 5percent B, 4.00 mins 100percent B, 4.30 mins 1percent B, 4.70 mins 1percent B.Flow rate 0.8 mL/min. Preparative HPLC: Phenomenex Gemini C18;250x21.2mmx10um; Acetonitrile:NH4OH eluting with a gradient specificto each compound (see below) over an 8?10 min gradient time.Flow rate 30/35 mL/min unless otherwise specified.
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