{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:50:16Z","timestamp":1760298616688},"reference-count":27,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2012,10,30]],"date-time":"2012-10-30T00:00:00Z","timestamp":1351555200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Journal of Peptide Science"],"published-print":{"date-parts":[[2012,12]]},"abstract":"<jats:p>The 4\u2010methoxybenzyloxymethyl (MBom) group was introduced at the <jats:italic>N<jats:sup>\u03c0<\/jats:sup><\/jats:italic>\u2010position of the histidine (His) residue by using a regioselective procedure, and its utility was examined under standard conditions used for the conventional and the microwave (MW)\u2010assisted solid phase peptide synthesis (SPPS) with 9\u2010fluorenylmethyoxycarbonyl (Fmoc) chemistry. The <jats:italic>N<jats:sup>\u03c0<\/jats:sup><\/jats:italic>\u2010MBom group fulfilling the requirements for the Fmoc strategy was found to prevent side\u2010chain\u2010induced racemization during incorporation of the His residue even in the case of MW\u2010assisted SPPS performed at a high temperature. In particular, the MBom group proved to be a suitable protecting group for the convergent synthesis because it remains attached to the imidazole ring during detachment of the protected His\u2010containing peptide segments from acid\u2010sensitive linkers by treatment with a weak acid such as 1% trifluoroacetic acid in dichloromethane. We also demonstrated the facile synthesis of Fmoc\u2010His(<jats:italic>\u03c0<\/jats:italic>\u2010MBom)\u2010OH with the aid of purification procedure by crystallization to effectively remove the undesired <jats:italic>\u03c4<\/jats:italic>\u2010isomer without resorting to silica gel column chromatography. This means that the present synthetic procedure can be used for large\u2010scale production without any obstacles. Copyright \u00a9 2012 European Peptide Society and John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/psc.2464","type":"journal-article","created":{"date-parts":[[2012,10,30]],"date-time":"2012-10-30T06:07:27Z","timestamp":1351577247000},"page":"763-769","update-policy":"http:\/\/dx.doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["Synthesis and application of <i>N<sup>\u03b1<\/sup><\/i>\u2010Fmoc\u2010<i>N<sup>\u03c0<\/sup><\/i>\u20104\u2010methoxybenzyloxymethylhistidine in solid phase peptide synthesis"],"prefix":"10.1002","volume":"18","author":[{"given":"Hajime","family":"Hibino","sequence":"first","affiliation":[{"name":"SAITO Research Center Peptide Institute, Inc.  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