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Table 1. Overview of the synthesized 1,2,5-benzothiadiazepin-4-on-1,1-dioxides. Yieldsare of purified material and are based upon the loading levels of the resin.O O OSNHR 1NR 2R 37 8R 1R 2Product Yield (%)a H Bn H H 26b Me Bn H H 38c (CH 2 ) 2 Ph Bn H H 54d i.Bu Bn H H 41e C 10 H 21 Bn H H 22f (CH 2 ) 2 N(CH 2 CH 2 )O Bn H H 33g H H H H 39h Me H H H 42i (CH 2 ) 2 Ph H H H 47j i.Bu H H H 32k C 10 H 21 H H H 10l (CH 2 ) 2 N(CH 2 CH 2 )O H H H 69m Me iBu H H 48n Me iBu Cl H 40o Me (CH 2 ) 4 NHBoc H H 54p Me CH 2 Im(Trt) H H 38q Me CH 2 indole(Boc) H H 57r Me Bn Cl H 23s Me Bn Br H 11t Me Bn H F 24u Me H Cl H 48v Me H Br H 56w Me H H F 61R 3Results and DiscussionIn Table 1 a list of synthesized benzothiadiazepines is outlined. Diversification of the targetheterocycles was achieved in three dimensions by using different amino acids (R 2 ),alcohols (R 1 ) and ortho-nosylchlorides (R 3 ).AcknowledgmentsWe would like to thank the “IWT - Agency for Innovation by Science and Technology” and GhentUniversity for financial support.References1. Evans, B.E., et al. J. Med. Chem. 31, 2235-2246 (1988).2. a) Horton, D.E., Bourne, G.T., Smythe, M.L. Chem. Rev. 103, 893-930 (2003); b) Costantino, L.,Barlocco, D. Curr. Med. Chem. 13, 65-85 (2006).3. a) Ogawa, K., Matsushita, Y. Chem. Pharm. Bull. 40, 2442-2447 (1992); b) Di Santo, R., Costi, R.,Artico, M., Ragno, R., Lavecchia, A., Novellino, E., Gavuzzo, E., La Torre, F., Cirilli, R., Cancio,R., Maga, G. Chem. Med. Chem. 1, 82-95 (2006).135
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Evaluation of Packing Materials Used for Preparative HPLCPurification of Peptide DerivativesKiyoshi Nokihara 1 , Takafumi Ohyama 1 , Noriko Ono 1 ,Kazuhiro Kitaori 2 , and Tetsuyuki Saika 31 HiPep Laboratories, Nakatsukasa-cho 486-46, Kamigyo-ku, Kyoto, 602-8158, Japan;2 DAISO GmbH, Immermannstrasse 13, 40210, Duesseldorf, Germany;3 DAISO CO., LTD., Ohtakasu-cho 9, Amagasaki-shi, Hyogo, 660-0842, JapanIntroductionWith increasing demands for pharmaceutical peptides, selection and evaluation of packingmaterials for HPLC, especially silica-based reverse phase, are of great interest for thepharmaceutical industries. Focusing on preparative separation of peptides and theirderivatives, several model peptides have been designed. These model peptides were usedfor separation-tests to compare the resolution of packing materials. The results were usedas a feedback to find optimal derivatization procedures for the silica surface. In addition toefficient removal of by-products from the target peptide, recovery of desired products isalso important for productivity. A GLP-1 analog, taspoglutide, consisting of 30 amino acidresidues containing non-natural AAs, was chosen as a model peptide for the recovery testand for comparison of commercially available column packing materials.H-Aib-EGTFTSDVSSYLEGQAAKEFIAWLVK-Aib-R-NH 2Fig. 1. Taspoglutide (TAS; glucagon-like peptide-1, GLP-1; mwt : 3339.74).Results and DiscussionBy-product containing peptides are often deletion peptides, which are found for sequencescontaining sterically hindered amino acids, cis-trans isomers of Pro-, succinimidyl Asp-,Met(O)-residues or degradation compounds caused by cleavage of Trp residues. Modelpeptides containing these by-products (Table 1) have been synthesized using conventionalFmoc-SPPS with HBTU and HOBt on an automated peptide synthesizer with low-costWang-resin in DMF. Cleaved peptides were characterized with a high resolution reversephase HPLC-column, HiPep-Cadenza (3 micron ODS, 3 i.d. X 150 mm), using on-line iontrapMS to identify the desired peptide and by-products. These model peptides were thenused for separation tests to compare the resolution, and results were used as a feedback tofind optimal derivatization procedures for the silica surface.Efficient removal of by-products from the target peptide on a large scale isindispensable and recovery of the desired products is important for productivity. A GLP-1analog, taspoglutide (TAS), consisting of 30 amino acid residues containing two Aibs, nonnaturalamino acid, was chosen as a model peptide for the recovery test and for comparisonof commercially available column packing materials. The synthesis of TAS (Figure 1) wascarried out using an automated synthesizer (PSSM8, Shimadzu), with HBTU and HOBt asTable 1. Design of model peptides containing by-productsBy-products Sequence of the target Mol. wt1 Deletion Peptides GQLKEALLDTG 1144.292 Cis-Trans isomer of Pro SPTRRELQVWG 1328.493 Succinimide from Asp LLDTGADDTVL 1132.234Degradates of Trpgenerated by cleavagePQITLWQRPLV 1350.635 Met(O) KPKMIGGIGGF 1104.38136
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Peptides 2010Tales of PeptidesProce
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Peptides 2010Tales of PeptidesProce
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IntroductionWe had the distinct hon
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Scientific programIn planning the 3
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31 st EUROPEAN PEPTIDE SYMPOSIUMSep
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published by John Wiley & Sons as a
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The Josef Rudinger AwardThis award
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Young Investigators' SymposiumThe y
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xxiv
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Design of Peptidyl-Inhibitors for G
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Synthetic Antifreeze Glycopeptide A
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Synthesis and Oxidative Folding of
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Convergent Syntheses of Huprp106-12
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Bactericidal Activity of Small Beta
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Bradykinin Analogues Acylated on Th
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Antimicrobial Activity of Small 3-(
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Interaction of Curcumin with A-Synu
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Fluorescent and Luminescent Fusion
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Cellular Expression of the Human An
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2D IR Spectroscopy of Oligopeptides
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large, non-redundant subset of prot
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The aberrantly glucosylated peptide
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Table 1. Proline cis/trans ratios o
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Table 1. Yields, UV-vis absorption
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Table 1. Purity of the targeted tri
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processes are blocked. Interestingl
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(tb4 n ,1 m )MTII(tb1 n ,4 m )MTIIF
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Fig. 2. a) Part of the 400 MHz HR-M
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Once printed, the amino acid partic
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A) PSA, few seconds73B) PSA, 45 min
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short β strands. In contrast, nume
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neg. control Cs9-Rhd MM-218Fig. 2.
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Table 1. The general structure of t
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% ID in the liver 1 h p.i.100908070
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Peptidyl phosphoranes were first re
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obtained from the same sardines and
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MccJ25 variants were produced by si
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Fig. 2. Proposed signaling mechanis
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Table 1. mCD4-HS12 antiviral activi
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Subject index(S)-2-(1-adamantyl)gly
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chip 18chiral triazine condensing r
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heat stress 348helical conformation
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O-acyl isopeptide method 112obesity
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SH2-ligands 210short collagen-relat
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Author indexAboye, Teshome Leta 142
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Chi, Hongfang 480Chiche, Laurent 6C
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Geronikaki, Athina 444Gessmann, Ren
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Kostova, Kalina 528Kotzia, Georgia
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Nagata, Koji 162Nagayev, Igor Yu. 5
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Salvarese, Nicola 518Sammet, Benedi
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Vauquelin, Georges 138Veiga, Ana Sa
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