title: Synthesis of optically active dodecaborate-containing L-amino acids for BNCT.
abstract: A convenient and simple synthetic method of dodecaboratethio-L-amino acid, a new class of tumor-seeking boron carrier for BNCT, was accomplished from S-cyanoethylthioundecahydro-closo-dodecaborate (S-cyanoethyl-(10)BSH, [(10)B(12)H(11)](2-)SCH(2)CH(2)CN) and bromo-L-α-amino acids by nearly one step S-alkylation. An improved synthesis of S-cyanoethyl-(10)BSH, a key starting compound for S-alkylation, was also performed by Michael addition of (10)BSH with acryronitrile in high yield. Four kinds of new dodecaboratethio-L-amino acids were obtained in optically pure form without the need for any optical resolution.
authors.affiliation: Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, Nakaku, Sakai, Japan.
authors.forename: Shintaro
authors.initials: S
authors.lastname: Kusaka
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Hattori
authors.forename: Kouki
authors.initials: K
authors.lastname: Uehara
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Asano
authors.forename: Shinji
authors.initials: S
authors.lastname: Tanimori
authors.forename: Mitsunori
authors.initials: M
authors.lastname: Kirihata
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis*; D001896:Boron Compounds / Q000737:chemistry*; D016754:Boron Neutron Capture Therapy; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D001896:Boron Compounds; C119788:dodecaborate