Total synthesis and membrane modifying properties of the lipopeptaibol trikoningin KB II and its analogues with acyl chains of different length at the N‐ and C‐termini

Trikoningin KB II, a ten‐amino acid residue lipopeptaibol blocked at the N‐terminus by the n‐octanoyl group and at the C‐terminus by the 1,2‐amino alcohol l ‐leucinol, and extracted from the fungus Trichoderma koningii, exhibits membrane‐modifying properties. We have synthesized by solution‐phase methods trikoningin KB II and several analogues with acyl chains of different length at the N‐ and C‐termini. Permeability measurements showed that an appropriate length of the linear acyl chain is a more important characteristic for the onset of significant membrane‐modifying activity than its position in the peptide chain. Copyright © 1999 European Peptide Society and John Wiley & Sons, Ltd.     

Synthesis of new C3 symmetric amino acid‐ and aminoalcohol‐containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3‐symmetric (R)‐phenylglycinol N‐1,3,5‐benzenetricarboxylic acid‐derived chiral high‐performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N‐3,5‐dintrobenzoyl (DNB) (R)‐phenylglycinol‐derived CSP. Over a decade ago, (S)‐leucinol, (R)‐phenylglycine, and (S)‐leucine derivatives were used as the starting materials of 3,5‐DNB‐based Pirkle‐type CSPs for chiral separation. In this study, three new C3‐symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3‐symmetric CSPs (CSP 2–CSP 4).     

Chiral separation on various modified amino alcohol‐derived HPLC chiral stationary phases

3,5‐Dinitrobenzoyl chloride was previously used for the preparation of (R)‐phenylglycinol‐ and (S)‐leucinol‐derived chiral stationary phases. In this study, 3,5‐bis(trifluoromethyl)benzoyl chloride, 2‐furoyl chloride, 2‐theonyl chloride, 10,11‐dihydro‐5H‐dibenzo[b,f]azepine‐5‐carbonyl chloride, diphenylcarbamoyl chloride, and 1‐adamantanecarbonyl chloride were used to prepare six new phenylglycinol‐derived chiral stationary phases (CSPs) and five new leucinol‐derived CSPs. Using these 11 CSPs, chiral separation of nine π‐acidic amino acid derivatives and five π‐basic compounds was performed, and the separation results were compared. An adamantyl‐derived CSP showed good separation. Chirality 28:276–281, 2016. © 2016 Wiley Periodicals, Inc.