{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T13:03:31Z","timestamp":1789909411704,"version":"4.0.1"},"reference-count":57,"publisher":"Wiley","issue":"48","license":[{"start":{"date-parts":[[2015,10,1]],"date-time":"2015-10-01T00:00:00Z","timestamp":1443657600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Grant-in-Aid for Scientific Research","award":["25220804"],"award-info":[{"award-number":["25220804"]}]},{"name":"Grant-in-Aid for Young Scientists (B)","award":["26810047"],"award-info":[{"award-number":["26810047"]}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"crossref"}]},{"name":"JSPS"},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology, Japan","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2015,11,23]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The dynamic planar chirality in a peptide\u2010bound Ni<jats:sup>II<\/jats:sup>\u2010salphen\u2010based macrocycle can be remotely controlled. First, a right\u2010handed (<jats:italic>P<\/jats:italic>)\u20103<jats:sub>10<\/jats:sub>\u2010helix is induced in the dynamic helical oligopeptides by a chiral amino acid residue far from the macrocyclic framework. The induced planar chirality remains dynamic in chloroform and acetonitrile, but is almost completely locked in fluoroalcohols as a result of the solvent\u2010induced transition of the peptide chains from a 3<jats:sub>10<\/jats:sub>\u2010helix to a wider \u03b1\u2010helix, which freezes the rotation of the pendant peptide units around the macrocycle.<\/jats:p>","DOI":"10.1002\/anie.201507918","type":"journal-article","created":{"date-parts":[[2015,10,1]],"date-time":"2015-10-01T12:36:53Z","timestamp":1443703013000},"page":"14442-14446","source":"Crossref","is-referenced-by-count":46,"title":["Remote Control of the Planar Chirality in Peptide\u2010Bound Metallomacrocycles and Dynamic\u2010to\u2010Static Planar Chirality Control Triggered by Solvent\u2010Induced 3<sub>10<\/sub>\u2010to\u2010\u03b1\u2010Helix Transitions"],"prefix":"10.1002","volume":"54","author":[{"given":"Fumihiko","family":"Mamiya","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Naoki","family":"Ousaka","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eiji","family":"Yashima","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,10]]},"reference":[{"key":"e_1_2_3_1_2","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-2836(65)80285-6"},{"key":"e_1_2_3_3_2","first-page":"163","volume-title":"Advances in Protein Chemistry and Structural Biology, Vol.\u200583","author":"Bu Z.","year":"2011"},{"key":"e_1_2_3_4_2","unstructured":"For examples of domino\u2010type chiral information transfer along achiral peptide backbones see:"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0026096"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017126w"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja040100v"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901892"},{"key":"e_1_2_3_8_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901892"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC03944K"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr990120t"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900162q"},{"key":"e_1_2_3_12_2","unstructured":"\u00a0"},{"key":"e_1_2_3_13_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1146"},{"key":"e_1_2_3_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300361"},{"key":"e_1_2_3_15_2","unstructured":"For reviews see:"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/b806203j"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar5000924"},{"key":"e_1_2_3_18_2","unstructured":"For a review see:"},{"key":"e_1_2_3_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr200077m"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja711260m"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1021508"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201302675"},{"key":"e_1_2_3_22_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201302675"},{"key":"e_1_2_3_23_2","unstructured":"For reviews on metallosalphen\u2010 or metallosalen\u2010based supramolecules see:"},{"key":"e_1_2_3_24_2","doi-asserted-by":"publisher","DOI":"10.1039\/b910989g"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15170C"},{"key":"e_1_2_3_26_2","unstructured":"1\u2010Aminocyclohexane\u20101\u2010carboxylic acid (Ac6c)[8a\u2013c]and \u03b1\u2010aminoisobutyric acid (Aib)[8d e]are known as strong helicogenic achiral amino acids; OTg=2\u2010(2\u2010(2\u2010methoxyethoxy)ethoxy)ethyl."},{"key":"e_1_2_3_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00280a038"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma00185a031"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma00185a032"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00481a001"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/0968-0004(91)90142-I"},{"key":"e_1_2_3_32_2","unstructured":"For the synthesis and characterization of the new peptide (n=6) the ligands (1\u20096merand2\u20098mer) and the macrocycles (3\u20096merand4\u20098mer) see the Supporting Information."},{"key":"e_1_2_3_33_2","unstructured":"For examples of stimuli\u2010responsive 310\u2010to\u2010\u03b1\u2010helix transitions see:"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199603261"},{"key":"e_1_2_3_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961080323"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja962875c"},{"key":"e_1_2_3_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351015"},{"key":"e_1_2_3_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200351015"},{"key":"e_1_2_3_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200502240"},{"key":"e_1_2_3_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200502240"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja076656a"},{"key":"e_1_2_3_39_2","unstructured":"This effect may be ascribed at least in part to the flexible \u2010OCH2\u2010 spacer between the pendant peptide chain and the phenylene unit which may disturb the efficient stereochemical communication between the macrocyclic moiety and the (P)\u2010310\u2010helical peptides. A similar non\u2010perfect diastereoselectivity has also been found in a pillar[5]arene bearing chiral substituents on both rims through the \u2010OCH2\u2010 spacer and the diastereomeric ratio pR\/pS(or pS\/pR) was reported to be 56.7:43.3 under conditions similar to those in the present study (CDCl3 25\u2009\u00b0C).[5c]"},{"key":"e_1_2_3_40_2","unstructured":"The diastereomeric ratio of4\u20098mercould not be determined by1H\u2005NMR spectroscopy even at low temperatures because of broadening of the signals and attempts to separate the diastereomers by HPLC were unsuccessful. However the diastereomeric ratio of4\u20098merseems to be similar to that of3\u20096merbecause their CD intensities and spectral patterns are almost identical."},{"key":"e_1_2_3_41_2","unstructured":"In accordance with the CD spectral changes the1H\u2005NMR signals of the terminal methoxy protons of3\u20096mersignificantly changed when measured in CDCl3and CD3CN mixtures and the major peak assigned to the (pR pR pR) or (pS pS pS) diastereomer in CDCl3decreased in intensity as the amount of CD3CN was increased; however the diastereomeric ratios could not be estimated owing to significant signal overlap (Figure\u2005S9)."},{"key":"e_1_2_3_42_2","unstructured":"The helix length was estimated by the energy\u2010minimized structure of the corresponding peptide in4\u20098mer(Figure\u20054\u2009b)."},{"key":"e_1_2_3_43_2","unstructured":"Their helix widths are identical (ca. 1.0\u2005nm; Figure\u20054\u2009a \u2009b)."},{"key":"e_1_2_3_44_2","unstructured":"For examples see:"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1097-0282(199609)39:3<279::AID-BIP1>3.0.CO;2-L"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja054452t"},{"key":"e_1_2_3_47_2","unstructured":"It has been reported that the efficiency of chiral information transmittance along an Aib\u2010based achiral peptide chain decreases with an increase in the solvent polarity;[2d e \u20093b]in other words the frequency of the helical reversal likely increases with increasing solvent polarity. In fact thek\u2005values of3\u20096merand4\u20098merat 25\u2009\u00b0C are much higher in a mixed polar solvent (CHCl3\/CH3CN=1:9 v\/v) than in the less polar CHCl3(Table\u2005S2)."},{"key":"e_1_2_3_48_2","unstructured":"The domino\u2010type chiral information transfer along the achiral peptide chain has been limited to dynamic 310\u2010helical peptides composed of achiral amino acid residues.[2a\u2013e]Therefore we have demonstrated for the first time that such a domino\u2010type chiral information transfer takes place along the dynamic \u03b1\u2010helical peptide chain; see the text below."},{"key":"e_1_2_3_49_2","unstructured":"This means that the remotely stereocontrolled planar chirality is diastereomerically \u201cmemorized\u201d although the pendant peptide chains possess the chiral residue. For recent examples of chiral memory effects see:"},{"key":"e_1_2_3_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja311738m"},{"key":"e_1_2_3_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja410117q"},{"key":"e_1_2_3_52_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1916"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201507918","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201507918","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.201507918","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201507918","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,29]],"date-time":"2023-08-29T09:00:29Z","timestamp":1693299629000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201507918"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,10]]},"references-count":57,"journal-issue":{"issue":"48","published-print":{"date-parts":[[2015,11,23]]}},"alternative-id":["10.1002\/anie.201507918"],"URL":"https:\/\/doi.org\/10.1002\/anie.201507918","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,10]]}}}