A Novel Approach to the Syntheses of Functionalized, Water-Soluble Icosahedral Carboranyl Anions. Crystal Structure of Methyl N-[(Trimethylamineboryl)carbonyl]-L-tyrosinate: A Synthon for Novel Carboranylpeptides

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Title:A Novel Approach to the Syntheses of Functionalized, Water-Soluble Icosahedral Carboranyl Anions. Crystal Structure of Methyl N-[(Trimethylamineboryl)carbonyl]-L-tyrosinate: A Synthon for Novel Carboranylpeptides
Creators:
Spielvogel, Bernard F.
Rana, Geeta
Vyakaranam, Kamesh
Grelck, Kurt
Dicke, Kari E.
Dolash, Bridget D.
Li, Shou-Jian
Zheng, Chong
Maguire, John A.
Takagaki, Masao
Hosmane, Narayan S.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 7, pp. 1095-1108
Uncontrolled Keywords:Peptides, Amino acids, BNCT, Amineboranes, Carboranes, Boron neutron capture therapy

Abstract

New functionalized water-soluble carboranyl anions have been prepared from <i>ortho</i>-carborane through lithiation and subsequent derivatization. The reaction of Li<sub>2</sub>[1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub>] with Me<sub>3</sub>NBH<sub>2</sub>X produced the carboranylborane dianions, [1,2-(BH<sub>2</sub>X)-1,2-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub>]<sup>2-</sup> (X = H (<strong>2a</strong>), CN (<strong>2b</strong>), COOMe (<strong>2c</strong>), COOH (<strong>2d</strong>)), while the reaction of [1-R-2-Li-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub>]<sup>-</sup> with Me<sub>3</sub>NBH<sub>2</sub>X produced the monoanions [1-R-2-BH<sub>2</sub>X-C<sub>2</sub>B<sub>10</sub>H<sub>10</sub>]<sup>-</sup> (R = C<sub>6</sub>H<sub>5</sub>, X = H (<strong>2e</strong>), CN (<strong>2f</strong>), COOH (<strong>2h</strong>), COOCH<sub>3</sub> (<strong>2g</strong>), CONHCH(CH<sub>2</sub>OH)COOMe (<strong>2i</strong>), CONHCH(CHMe<sub>2</sub>)COOMe (<strong>2j</strong>), CONHCH(4-CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>OH)- COOMe (<strong>2k</strong>); R = Me, X = H (<strong>2l</strong>), COOH (<strong>2m</strong>)). These water-soluble carboranylboranes have the potential of being effective hydrophilic boron neutron capture therapy (BNCT) agents. The crystal structure of the peptide precursor Me<sub>3</sub>NBH<sub>2</sub>CONHCH(4-CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>OH)COOMe (<strong>3b</strong>) which showed a special promise as a BNCT agent is also described. <p>

Title:A Novel Approach to the Syntheses of Functionalized, Water-Soluble Icosahedral Carboranyl Anions. Crystal Structure of Methyl N-[(Trimethylamineboryl)carbonyl]-L-tyrosinate: A Synthon for Novel Carboranylpeptides
Creators:
Spielvogel, Bernard F.
Rana, Geeta
Vyakaranam, Kamesh
Grelck, Kurt
Dicke, Kari E.
Dolash, Bridget D.
Li, Shou-Jian
Zheng, Chong
Maguire, John A.
Takagaki, Masao
Hosmane, Narayan S.
Uncontrolled Keywords:Peptides, Amino acids, BNCT, Amineboranes, Carboranes, Boron neutron capture therapy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:7
Page Range:pp. 1095-1108
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021095UNSPECIFIED
ID Code:1975
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Spielvogel, Bernard F.; Rana, Geeta; Vyakaranam, Kamesh; Grelck, Kurt; Dicke, Kari E.; Dolash, Bridget D.; Li, Shou-Jian; Zheng, Chong; Maguire, John A.; Takagaki, Masao; Hosmane, Narayan S. (2002) A Novel Approach to the Syntheses of Functionalized, Water-Soluble Icosahedral Carboranyl Anions. Crystal Structure of Methyl N-[(Trimethylamineboryl)carbonyl]-L-tyrosinate: A Synthon for Novel Carboranylpeptides. Collection of Czechoslovak Chemical Communications, 67 (7). pp. 1095-1108. ISSN 0010-0765

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