{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2024,1,2]],"date-time":"2024-01-02T16:22:27Z","timestamp":1704212547147},"reference-count":32,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2015,9,1]],"date-time":"2015-09-01T00:00:00Z","timestamp":1441065600000},"content-version":"tdm","delay-in-days":427,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Pept. Sci."],"published-print":{"date-parts":[[2014,10]]},"DOI":"10.1002\/psc.2668","type":"journal-article","created":{"date-parts":[[2014,7,2]],"date-time":"2014-07-02T07:56:55Z","timestamp":1404287815000},"page":"794-802","source":"Crossref","is-referenced-by-count":7,"title":["Modulating the structure of phenylalanine-incorporated ascidiacyclamide through fluorination"],"prefix":"10.1002","volume":"20","author":[{"given":"Akiko","family":"Asano","sequence":"first","affiliation":[{"name":"Osaka University of Pharmaceutical Sciences; 4-20-1, Nasahara Takatsuki Osaka 569-1094 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takeshi","family":"Yamada","sequence":"additional","affiliation":[{"name":"Osaka University of Pharmaceutical Sciences; 4-20-1, Nasahara Takatsuki Osaka 569-1094 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mitsunobu","family":"Doi","sequence":"additional","affiliation":[{"name":"Osaka University of Pharmaceutical Sciences; 4-20-1, Nasahara Takatsuki Osaka 569-1094 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,7,1]]},"reference":[{"key":"10.1002\/psc.2668-BIB0001|psc2668-cit-0001","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1039\/c39830000323","article-title":"A new cyclic peptide, ascidiacyclamide, isolated from ascidian","author":"Hamamoto","year":"1983","journal-title":"Chem. Commun."},{"key":"10.1002\/psc.2668-BIB0002|psc2668-cit-0002","doi-asserted-by":"crossref","first-page":"370","DOI":"10.1039\/c39870000370","article-title":"X-ray crystal structure of ascidiacyclamide, a cytotoxic cyclic peptide from ascidian","author":"Ishida","year":"1987","journal-title":"Chem. Commun."},{"key":"10.1002\/psc.2668-BIB0003|psc2668-cit-0003","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1021\/jo00236a022","article-title":"Solution and solid-state conformations of ascidiacyclamide, a cytotoxic cyclic peptide from ascidian","volume":"53","author":"Ishida","year":"1988","journal-title":"J. Org. Chem."},{"key":"10.1002\/psc.2668-BIB0004|psc2668-cit-0004","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1002\/bip.360320204","article-title":"Molecular conformation of ascidiacyclamide, a cytotoxic cyclic peptide from ascidian: X-ray analyses of its free from and solvate crystals","volume":"32","author":"Ishida","year":"1992","journal-title":"Biopolymers"},{"key":"10.1002\/psc.2668-BIB0005|psc2668-cit-0005","doi-asserted-by":"crossref","first-page":"3463","DOI":"10.1021\/jo00275a036","article-title":"Cyclic peptides from the ascidian Lissoclinum patella: conformational analysis of patellamide D by X-ray analysis and molecular modeling","volume":"54","author":"Schmiz","year":"1989","journal-title":"J.Org. Chem."},{"key":"10.1002\/psc.2668-BIB0006|psc2668-cit-0006","doi-asserted-by":"crossref","first-page":"1686","DOI":"10.1248\/cpb.41.1686","article-title":"Molecular conformation of patellamide A, a cytotoxic cyclic peptide from the ascidian Lissoclinum patella, by X-ray crystal analysis","volume":"41","author":"In","year":"1993","journal-title":"Chem. Pharm. Bull."},{"key":"10.1002\/psc.2668-BIB0007|psc2668-cit-0007","doi-asserted-by":"crossref","first-page":"459","DOI":"10.1002\/(SICI)1097-0282(199905)49:6<459::AID-BIP4>3.0.CO;2-G","article-title":"Conformational change of ascidiacyclamide caused by asymmetric modification for an isoleucine residue: structural analyses of [Gly], [Leu], and [Phe] ascidiacyclamide by X-ray diffraction and NMR spectroscopy","volume":"49","author":"Doi","year":"1999","journal-title":"Biopolymers"},{"key":"10.1002\/psc.2668-BIB0008|psc2668-cit-0008","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1002\/1097-0282(200103)58:3<295::AID-BIP1006>3.0.CO;2-X","article-title":"Effects of amino acids and chirality for molecular folding of desoxazoline-ascidiacyclamide derivatives: x-ray crystal structures of four cyclic octapeptides including unusual amino acids, cyclo(-Ile-aThr-Val-Thz-)2, cyclo(-Ala-aThr-D-Val-Thz-Ile-aThr-D-Val-Thz-), cyclo(-Val-aThr-D-Val-Thz-Ile-aThr-D-Val-Thz-), and cyclo(-Ile-aThr-Val-Thz-Ile-aThr-D-Val-Thz-)","volume":"58","author":"Asano","year":"2001","journal-title":"Biopolymers"},{"key":"10.1002\/psc.2668-BIB0009|psc2668-cit-0009","first-page":"o1019","article-title":"A folded conformation of an ascidiacyclamide derivative: 3-methoxysulfoxide-(2R,3R)-threoninyl desoxazoline-ascidiacyclamide","volume":"E57","author":"Doi","year":"2001","journal-title":"Acta Crystallogr."},{"key":"10.1002\/psc.2668-BIB0010|psc2668-cit-0010","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1034\/j.1399-3011.2002.02981.x","article-title":"Effect of asymmetric modification on the conformation of ascidiacyclamide analogs","volume":"60","author":"Asano","year":"2002","journal-title":"J. Peptide Res."},{"key":"10.1002\/psc.2668-BIB0011|psc2668-cit-0011","doi-asserted-by":"crossref","first-page":"3372","DOI":"10.1016\/j.bmc.2011.04.036","article-title":"The square conformation of phenylglycine-incorporated ascidiacyclamide is stabilized by CH\/\u03c0 interactions between amino acid side chains","volume":"19","author":"Asano","year":"2011","journal-title":"Bioorg. Med. Chem."},{"key":"10.1002\/psc.2668-BIB0012|psc2668-cit-0012","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1039\/b201097f","article-title":"Fluorinated amino acid in protein design and engineering","volume":"31","author":"Yoder","year":"2002","journal-title":"Chem. Soc. Rev."},{"key":"10.1002\/psc.2668-BIB0013|psc2668-cit-0013","doi-asserted-by":"crossref","first-page":"4483","DOI":"10.1002\/ejoc.200500205","article-title":"Fluorine in peptide design and protein engineering","volume":"21","author":"Jaeckel","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"10.1002\/psc.2668-BIB0014|psc2668-cit-0014","doi-asserted-by":"crossref","first-page":"15932","DOI":"10.1021\/ja0634573","article-title":"Stabilizing and destabilizing of phenylalanine\u2009\u2192\u2009F5-phenylalanine mutations on the folding of a small protein","volume":"128","author":"Matthew","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/psc.2668-BIB0015|psc2668-cit-0015","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1002\/bip.21594","article-title":"Probing phenylalanine environments in oligomeric structures with pentafluorophenylalanine and cyclohexylalanine","volume":"95","author":"Nomura","year":"2011","journal-title":"Biopolymers"},{"key":"10.1002\/psc.2668-BIB0016|psc2668-cit-0016","doi-asserted-by":"crossref","first-page":"666","DOI":"10.1038\/33573","article-title":"Code for collagen's stability deciphered","volume":"392","author":"Holmgren","year":"1998","journal-title":"Nature"},{"key":"10.1002\/psc.2668-BIB0017|psc2668-cit-0017","doi-asserted-by":"crossref","first-page":"2790","DOI":"10.1021\/bi0022588","article-title":"Stabilization of coiled-coil peptide domains by introduction of trifluoroleucine","volume":"40","author":"Tang","year":"2001","journal-title":"Biochemistry"},{"key":"10.1002\/psc.2668-BIB0018|psc2668-cit-0018","doi-asserted-by":"crossref","first-page":"4393","DOI":"10.1021\/ja002961j","article-title":"A coiled coil with fluorous core","volume":"123","author":"Bilgicer","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/psc.2668-BIB0019|psc2668-cit-0019","doi-asserted-by":"crossref","first-page":"11815","DOI":"10.1021\/ja016767o","article-title":"Programmed self-sorting of coiled coil with leucine and hexafluoroleucine cores","volume":"123","author":"Bilgicer","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/psc.2668-BIB0020|psc2668-cit-0020","doi-asserted-by":"crossref","first-page":"9286","DOI":"10.1021\/ja0353199","article-title":"\u03d5-values beyond the ribosomally encoded amino acids: kinetic and thermodynamic consequences of incorporating trifluoromethyl amino acids in a globular protein","volume":"125","author":"Horng","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/psc.2668-BIB0021|psc2668-cit-0021","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1021\/ja0563410","article-title":"Modulating protein structure with fluorous amino acids: increased stability and native-like structure conferred on a 4-helix bundle protein by hexafluoroleucine","volume":"128","author":"Lee","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/psc.2668-BIB0022|psc2668-cit-0022","doi-asserted-by":"crossref","first-page":"16277","DOI":"10.1021\/bi049086p","article-title":"Fluorous effect in proteins: de novo design and characterization of a four-\u03b1-helix bundle protein containing hexafluoroleucine","volume":"43","author":"Lee","year":"2004","journal-title":"Biochemistry"},{"key":"10.1002\/psc.2668-BIB0023|psc2668-cit-0023","doi-asserted-by":"crossref","first-page":"4198","DOI":"10.1002\/anie.200504387","article-title":"Fluorine in a native protein environment - how the spatial demand and polarity of fluoroalkyl groups affect protein folding","volume":"45","author":"Jaeckel","year":"2006","journal-title":"Angew. Chem. Int. Ed."},{"key":"10.1002\/psc.2668-BIB0024|psc2668-cit-0024","doi-asserted-by":"crossref","first-page":"3223","DOI":"10.1016\/S0040-4039(00)98157-7","article-title":"New methods and reagents in organic synthesis. 51. A synthesis of ascidiacyclamide, a cytotoxic cyclic peptide from ascidian-determination of its absolute configuration","volume":"26","author":"Hamada","year":"1985","journal-title":"Tetrahedron Lett."},{"key":"10.1002\/psc.2668-BIB0025|psc2668-cit-0025","doi-asserted-by":"crossref","first-page":"1252","DOI":"10.1021\/jo00383a014","article-title":"New methods and reagents in organic synthesis. 67. A general synthesis of derivatives of optically pure 2-(1-aminoalkyl) thiazole-4-carboxylic acids","volume":"52","author":"Hamada","year":"1987","journal-title":"J. Org. Chem."},{"key":"10.1002\/psc.2668-BIB0026|psc2668-cit-0026","doi-asserted-by":"crossref","first-page":"4497","DOI":"10.1016\/0006-2952(89)90662-X","article-title":"Mechanistic aspects of the cytocidal action of ulithiacyclamide on mouse leukemia L1210 cells in vitro","volume":"38","author":"Kohda","year":"1989","journal-title":"Biochem. Pharmacol."},{"key":"10.1002\/psc.2668-BIB0027|psc2668-cit-0027","doi-asserted-by":"crossref","first-page":"4500","DOI":"10.1016\/0006-2952(89)90663-1","article-title":"Ulicyclamide is cytotoxic against L1210 cells in vitro and inhibits both DNA and RNA syntheses","volume":"38","author":"Kohda","year":"1989","journal-title":"Biochem. Pharmacol."},{"key":"10.1002\/psc.2668-BIB0028|psc2668-cit-0028","doi-asserted-by":"crossref","first-page":"2648","DOI":"10.1021\/ja00060a013","article-title":"CH-\u03c0 interaction as an important driving force of host-guest complexation in apolar organic media. Binding of monools and acetylated compounds to resorcinol cyclic tetramer as studied by proton NMR and circular dichroism spectroscopy","volume":"115","author":"Kobayashi","year":"1993","journal-title":"J. Am. Chem. Soc."},{"key":"10.1002\/psc.2668-BIB0029|psc2668-cit-0029","doi-asserted-by":"crossref","first-page":"428","DOI":"10.1006\/bbrc.1993.1641","article-title":"Water-soluble chymotrypsin specific inhibitors containing arginine","volume":"193","author":"Maeda","year":"1993","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"10.1002\/psc.2668-BIB0030|psc2668-cit-0030","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/S0006-291X(02)02088-0","article-title":"A flat squared conformation of an ascuduacyclamide derivative caused by chiral modification of an oxazoline residue","volume":"297","author":"Asano","year":"2002","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"10.1002\/psc.2668-BIB0031|psc2668-cit-0031","first-page":"o488","article-title":"cyclo(-Cha-Oxz-D-Val-Thz-Ile-Oxz-D-Val-Thz-) N, N-dimethyl-acetamide dehydrate: a square form of cyclohexylalanine-incorporated ascidiacyclamide having the strongest cytotoxicity","volume":"C59","author":"Asano","year":"2003","journal-title":"Acta Crystallogr."},{"issue":"Suppl. 1","key":"10.1002\/psc.2668-BIB0032|psc2668-cit-0032","doi-asserted-by":"crossref","first-page":"90","DOI":"10.1111\/j.1747-0285.2006.00345.x","article-title":"Conformational restraints induced by modification of configuration of threonine and oxazoline residues in ascidiacyclamide analogues","volume":"66","author":"Asano","year":"2006","journal-title":"J. Peptide Res."}],"container-title":["Journal of Peptide Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fpsc.2668","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full\/10.1002\/psc.2668","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,7,4]],"date-time":"2021-07-04T20:34:34Z","timestamp":1625430874000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/psc.2668"}},"subtitle":["MODULATING THE STRUCTURE OF PHE-INCORPORATED ASC THROUGH FLUORINATION"],"short-title":[],"issued":{"date-parts":[[2014,7,1]]},"references-count":32,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2014,10]]}},"URL":"https:\/\/doi.org\/10.1002\/psc.2668","relation":{},"ISSN":["1075-2617"],"issn-type":[{"value":"1075-2617","type":"print"}],"subject":[],"published":{"date-parts":[[2014,7,1]]}}}