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Table 1. Purity of the targeted tripeptides after coupling reactions of Boc-derivatives ontoa Gly-Phe bound on resin dipeptide. Two (2) reactions were performed in water usingmicrowave technology (TentaGel or ChemMatrix resin, EDC/HONB (5eq), 70 o C; 7min)DerivativeStarting materialH 2 N- GFTargeted tripeptideBoc-aa -GFBoc-Ala-OH - 99.4%Boc-Arg(Tosyl)-OH - 100%Boc-Cys(Acm)-OH - 96%Boc-Gly-OH - 100%Boc-Leu-OH - 98%Boc-Lys(2ClZ)-OH - 96%Boc-Lys(Alloc)-OH - 93%Boc-Phe-OH - 97%Boc-Pro-OH - 100%Boc-Ser-OH - 94%Boc-Trp-OH - 97%Boc-Tyr-OH - 97%Boc-Val-OH - 92%Boc-Asn(Bzl)-OH 35% 54%Boc-Asp(OBzl)-OH 11% 84%Boc-Gln(Bzl)-OH 23% 61%Boc-Glu(OBzl)-OH 14% 78%Boc-His(Tosyl)-OHn.d.Boc-Ile-OH - 83%Boc-Met-OH 3% 87%Boc-Thr(Bzl)-OH - 88%used for side chain protection, almost all provided complete reactions and high yield andpurity targeted tripeptides. Thus, alternative side chain protected derivatives are underinvestigation for their efficiency for coupling reactions in water at elevated temperature.Another critical issue was the use of the zwiterronic detergent TritonX100 that enhancesthe swelling properties of the poly (ethylenglycol) type resin and increases the solubility ofthe peptides.In order to study if this novel strategy can be applied using conventional thermalheating, coupling reaction of Boc-derivatives were performed using a hot plate, applyingthe same temperature as in the microwave promoted coupling. Similar results wereobtained. In conclusion, SPPS can be applied using water as solvent at elevated temperature(by thermal or microwave heating) and further studies are essential in order to optimize thecoupling reaction efficiency in water. The synthesis of the Leu-Enk pentapeptide has beensuccessfully performed using this new developed environmental friendly strategy [2].AcknowledgmentsA.S.G. acknowledges a MARIE-CURIE Intra-European-Fellowship- Project No 040451.References1. Galanis, A.S., Albericio, F., Grøtli, M. (Hilkka Lankinen Eds.) Peptides 2008 (Proceedings of the30th European Peptide Symposium), Finland, 2008, pp. 164-165.2. Galanis, A.S., Albericio, F., Grøtli, M. Org. Lett. 11, 4488-4491 (2009).11
Proceedings of the 31 st European Peptide SymposiumMichal Lebl, Morten Meldal, Knud J. Jensen, Thomas Hoeg-Jensen (Editors)European Peptide Society, 2010Bis-Azobenzene Photoswitchable α-Amino Acids forNanomaterials ApplicationsAlessandro Moretto 1 , Marco Crisma 1 , Paola Fatás 2 , Gema Ballano 2 ,Ana I. Jimenéz 2 , Carlos Cativiela 2 , and Claudio Toniolo 11 ICB, Padova Unit, CNR, Department of Chemistry, University of Padova, Padova, 35131,Italy; 2 Department of Organic Chemestry, ICMA, University of Zaragoza-CSIC,Zaragoza, 50009, SpainIntroductionThe photoisomerization of an azobenzene moiety between the extended (trans) andcompact (cis) conformations (Figure 1) is reversibly triggered by light at two differentwavelengths [1-3]. The resulting modifications in the molecular 3D-structures have beenextensively exploited to photoswitch transformation in chemical species reversibly forvarious types of applications, e.g. in the construction of optoelectronic devices [4].N NNN NNN NHONHHONH 22 OOtranscisFig. 1. The trans and cis forms of the C α -tetrasubstituted α-amino acid pAzoDbgsynthesized and studied in this work.Results and DiscussionHere, we describe synthesis and chemical characterization of the two achiral,C α -tetrasubstituted, α-amino acids, each characterized by two azobenzene moietiescovalently linked to their α-carbon atom, bis[4-(phenylazo)benzyl]Gly (pAzoDbg) and its3-(phenylazo)benzyl (mAzoDbg) analogue. These “albatros-like” compounds werecharacterized by UV-Vis spectroscopy and, one of them, by X-ray diffraction as well.We found that both compounds undergo multiple, reversible isomerizations in avariety of solvents by irradiation with Vis light (to trans) or UV light (to cis) (Figure 2).However, when the α-amino acids are dispersed in a paraffin medium, their photoswitchFig. 2. Mechanism of light-driven, trans/cis isomerization via the intermediate (X)-HpAzoDbg-L-Leu-OMe(cis-trans)/(Y)-H-pAzoDbg-L-Leu-OMe (trans-cis) diastereomers.12
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Peptides 2010Tales of PeptidesProce
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Peptides 2010Tales of PeptidesProce
Page 8 and 9: IntroductionWe had the distinct hon
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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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