Simple, high-yield synthesis of polyhedral carborane amino acids

Journal Article · Wed Feb 07 04:00:00 EST 1996 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja9534260· OSTI ID:223552

Kahl, S B; Kasar, R A ^[1]

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1. Univ. of California, San Francisco, CA (United States)

Boron neutron capture therapy (BNCT) is a form of binary cancer therapy that offers the potential of delivering spatially selective, high linear energy transfer radiation to the target cells while sparing surrounding normal tissue. We have demonstarted a versatile, general method for the conversion of o- ,m-, and p-carborane to their corresponding Boc-protected amino acids. Heterobifunctional polyhedral carboranes are exceedingly rare in the literature, and the amino acids prepared by this general method may prove to be valuable synthons for use in the synthesis of tumor-seeking compounds for BNCT or PDT. Morever, these conformationally constrained amino acids should be particularly interesting for use in peptide synthesis. The dihedral angle between the carbon atoms of these polyhedra increases in the order 60{degree} (ortho), 110{degree} (meta), and 180{degree} (para), allowing the peptide chemist to select a desired conformation. 11 refs.

• OSTI ID: 223552
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 5 Vol. 118; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
55 BIOLOGY AND MEDICINE
BASIC STUDIES
AMINO ACIDS
BORON COMPLEXES
CARBORANES
NEOPLASMS
NEUTRON CAPTURE THERAPY
STRUCTURAL CHEMICAL ANALYSIS
SYNTHESIS