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Segment Coupling to a Highly Hindered N-Terminal, Alamethicin-Related alpha-Aminoisobutyric Acid (Aib) Residue |
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| Authors: | Carpino Louis A Abdel-Maksoud Adel Ali Mansour E M E Zewail Mohamed A |
| Affiliation: | a Department of Chemistry, University of Massachusetts, Amherst MA 01003, USA b Protein Research Department, Genetic Engineering Institute, Mubarak City for Scientific Research, Borg El-Arab, Alexandria 21934, Egypt c Department of Chemistry, Faculty of Science, Alexandria University, Alexandria 21321, Egypt d Peptide Chemistry Department, National Research Center, El-Tahrir St., Dokki, Cairo 12622, Egypt |
| Abstract: | A model [6+5] segment coupling process involving a C-terminal valine hexapeptide acid and a resin-attached pentapeptide amide, which N-terminated in a hindered Aib unit, was examined using a variety of HOAt-derived coupling reagents. Best results were observed with N-HAPyU in DCM solvent in which loss of configuration amounted to 5.8%. |
| Keywords: | Aib, α-aminoisobutyric acid residue Boc, tert-butyloxycarbonyl DCC, dicyclohexylcarbodiimide DB(DMAP), 2,6-di-t-butyl-4-(dimethylamino)pyridine DCM, dichloromethane DIC, N,N&prime -diisopropylcarbodiimide DIEA, N,N-diisopropylethylamine DMF, N,N-dimethylformamide Fmoc, 9-fluorenemethyloxycarbonyl N-HAPyU, 1-(dipyrrolidinylmethylene)-1H-1,2,3-triazolo [4,5-b] pyridinium hexafluorophosphate 3-oxide N-HATU, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b] pyridinium hexafluorophosphate 3-oxide PS, proton sponge, 1,8-bis(dimethylamino)naphthalene N-TBTU, 1-[bis(dimethylamino)methylene]-1H-benzotriazolium tetrafluoroborate 3-oxide TMP, 2,4,6-trimethylpyridine TFA, trifluoroacetic acid |
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