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Streptolidine

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Streptolidine
Names
IUPAC name (4S)-2-amino-5--4,5-dihydro-1H-imidazole-4-carboxylic acid
Other names Roseonine, AC1MIYK9
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
InChI
  • 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
SMILES
  • C(C(C1C(N=C(N1)N)C(=O)O)O)N
Properties
Chemical formula C6H12N4O3
Molar mass 188.187 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

Synthesis

Syntheses have been accomplished from D-ribose and D-xylose.

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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