Streptolidine
Names
IUPAC name
(4S)-2-amino-5-[(1R)-2-amino-1-hydroxyethyl]-4,5-dihydro-1H-imidazole-4-carboxylic acid
Other names
Roseonine, AC1MIYK9
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H12N4O3/c7-1-2(11)3-4(5(12)13)10-6(8)9-3/h2-4,11H,1,7H2,(H,12,13)(H3,8,9,10)
    Key: BQSPOPBPQURHDF-UHFFFAOYSA-N
  • C(C(C1C(N=C(N1)N)C(=O)O)O)N
Properties
C6H12N4O3
Molar mass 188.187 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Streptolidine is an amino acid isolated from the hydrolyzate of the Streptomyces antibiotics streptothricin and streptolin.[1] Its structure was first elucidated by chemical degradation[2] and later by x-ray crystallography.[3]

Synthesis

Syntheses have been accomplished from D-ribose[4] and D-xylose.[5]

References

  1. ^ Carter, H. E.; Sweeley, C. C.; Daniels, E. E.; McNary, J. E.; Schaffner, C. P.; West, C. A.; Van Tamelen, E. E.; Dyer, J. R.; Whaley, H. A. (20 October 1961). "Streptothricin and Streptolin: The Structure of Streptolidine (Roseonine)". Journal of the American Chemical Society. 83 (20): 4296–4297. doi:10.1021/ja01481a052.
  2. ^ Hanessian, Stephen (1983). Total Synthesis of Natural Products: The 'Chiron' Approach. Pergamon press. p. 173. ISBN 978-0-08-029247-2.
  3. ^ Bycroft, B. W.; King, T. J. (1 January 1972). "Crystal structure of streptolidine, a guanidine-containing amino-acid". Journal of the Chemical Society, Chemical Communications (11): 652. doi:10.1039/C39720000652.
  4. ^ Kusumoto, Shoichi, Shinichi Tsuji, and Tetsuo Shiba (1974). "Synthesis of streptolidine (roseonine, geamine)". Bulletin of the Chemical Society of Japan. 47 (11): 2690–2695. doi:10.1246/bcsj.47.2690.((cite journal)): CS1 maint: multiple names: authors list (link)
  5. ^ Kusumoto, Shoichi; et al. (1976). "Synthesis of streptolidine from D-xylose". Bulletin of the Chemical Society of Japan. 49 (12): 3611–3614. doi:10.1246/bcsj.49.3611.


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