Streptolidine Explained

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]

Notes and 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.. Journal of the American Chemical Society. 20 October 1961. 83. 20. 4296–4297. 10.1021/ja01481a052. Streptothricin and Streptolin: The Structure of Streptolidine (Roseonine).
2. Book: Hanessian, Stephen. Total Synthesis of Natural Products: The 'Chiron' Approach. 1983. Pergamon press. 978-0-08-029247-2. 173.
3. Bycroft. B. W.. King, T. J.. Crystal structure of streptolidine, a guanidine-containing amino-acid. Journal of the Chemical Society, Chemical Communications. 1 January 1972. 11. 652. 10.1039/C39720000652.
4. Kusumoto, Shoichi, Shinichi Tsuji, and Tetsuo Shiba . Synthesis of streptolidine (roseonine, geamine) . Bulletin of the Chemical Society of Japan . 47 . 11 . 1974 . 2690–2695 . 10.1246/bcsj.47.2690. free .
5. Synthesis of streptolidine from D-xylose . Bulletin of the Chemical Society of Japan . 49 . 12 . 1976 . 3611–3614 . 10.1246/bcsj.49.3611 . Kusumoto, Shoichi . etal . free .