9-BBN: An amino acid protecting group for functionalization of amino acid side chains in organic solvents.
9-Borabicyclononane (9-BBN) has been utilized to protect functionalized amino acids for potential chemoselective side chain manipulation. The 9-BBN group imparts organic solubility to otherwise hydrophilic molecules and is tolerant of a wide range of reaction conditions. The high degree of solubility of these molecules in THF is particularly noteworthy. It is cleaved with either aqueous HCl or by exchange with ethylenediamine in methanol. [reaction: see text]
Dent
William H
WH
Discovery Research, Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, IN 46268-1054, USA..
Erickson
W Randal
WR
Fields
Stephen C
SC
Parker
Marshall H
MH
Tromiczak
Eric G
EG
D000596:Amino Acids / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D007202:Indicators and Reagents; D009952:Ornithine / Q000031:analogs & derivatives / Q000737:chemistry; D012995:Solubility; D012997:Solvents
D000596:Amino Acids; D001896:Boron Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D012997:Solvents; C454803:9-borabicyclononane; D009952:Ornithine