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Determination of the absolute-configuration of (+)-neopentyl-1-d alcohol by neutron and x-ray-diffraction analysis

Academic Article
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Overview

authors

  • Yuan, H. S. H.
  • Stevens, Raymond
  • Bau, R.
  • Mosher, H. S.
  • Koetzle, T. F.

publication date

  • December 1994

journal

  • Proceedings of the National Academy of Sciences of the United States of America  Journal

abstract

  • The absolute configuration of (+)-neopentyl-1-d alcohol, prepared by the reduction of 2,2-dimethylpropanal-1-d by actively fermenting yeast, has been determined to be S by neutron diffraction. The neutron study was carried out on the phthalate half ester of neopentyl-1-d alcohol, crystallized as its strychnine salt. The absolute configuration of the (-)-strychninium cation was first determined by an x-ray anomalous dispersion study of its iodide salt. The chiral skeleton of strychnine then served as a reference from which the absolute configuration of the -O-CHD-C(CH3)3 group of neopentyl phthalate was determined. Difference Fourier maps calculated from the neutron data showed unambiguously that the -O-CHD-C(CH3)3 groups of both independent molecules in the unit cell had the S configuration. This work proves conclusively that the yeast system reduces aldehydes by delivering hydrogen to the re face of the carbonyl group. Crystallographic details: (-)-strychninium (+)-neopentyl-1-d phthalate, space group P2(1) (monoclinic), a = 18.564(6) A, b = 7.713(2) A, c = 23.361(8) A, beta = 94.18(4) degrees, V = 3336.0(5) A3, Z = 2 (T = 100 K). Final agreement factors are R(F) = 0.073 for 2768 reflections collected at room temperature (x-ray analysis) and R(F) = 0.144 for 960 reflections collected at 100 K (neutron analysis).

subject areas

  • Crystallography, X-Ray
  • Molecular Structure
  • Neutrons
  • Phthalic Acids
  • Strychnine
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Research

keywords

  • ALCOHOL DEHYDROGENASE
  • CHIRAL METHYLENE GROUP
  • DEUTERATED NEOPENTANOL
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Identity

International Standard Serial Number (ISSN)

  • 0027-8424

Digital Object Identifier (DOI)

  • 10.1073/pnas.91.26.12872

PubMed ID

  • 7809138
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Additional Document Info

start page

  • 12872

end page

  • 12876

volume

  • 91

issue

  • 26

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