Amino Acids

Dent, W. H.; Erickson, W. R.; Fields, S. C.; Parker, M. H.; Tromiczak, E. G. "Preparation and Utility of 9-BBN-Protected Amino Acids for Functionalization of Amino Acid Sidechains". Org. Chem. Lett. 2002, 1241.

Abstract:  9-Borabicyclononane (9-BBN) derivs. of amino acids I [R = (CH2)4NH2, (CH2)3NH2, CH2C6H4OH-4, CH2OH, CH2SH, CH2CO2H, (CH2)3NHC(:NH)NH2] have been prepd. The 9-BBN group imparts org. soly. to otherwise hydrophilic mols. and is tolerant of a wide range of reaction conditions. The high degree of soly. of these mols. in THF is particularly noteworthy. I is cleaved with either aq. HCl or by exchange with ethylenediamine in methanol.

Fields, Stephen Craig "Synthesis of optically active α-alkyl-α-amino acids via boroxazolidinones. (1990), 285 pp. CAN 115:115053 AN 1991:515053

Abstract:  Ph.D. thesis at the University of Wisconsin-Madison, 1990.

Erickson, W. R. "Streptonigrin Biosynthesis 9. Isolation of 4 Aminoanthranilic Acid: A New Shikimate Pathway Product From Streptomyces flocculus." J. Antibiot. 1988, 41, 688.

Abstract:  Incubation of S. flocculus with erythrose results in a 0.22% incorporation into 4 aminoanthranilic acid, a natural product not previously observed in nature. Additional incubation yielded streptonigrin, whereas acetylation gave the bisacetamide.