Anti-Infectives from Nature - Natural Products Chemistry: Sources, Separations, and Structures - page 100

SUMMARY
In this chapter, we give examples of several important naturally produced anti-
infective compounds. These are compounds are produced by microorganisms under
fermented conditions. They include the β-lactam antibiotics (e.g., penicillin, cepha-
losporin), erythromycin, the avermectins, and tetracyclines.
QUESTIONS
1. Why is IR spectroscopy useful for penicillin compounds?
2. Why is IR spectroscopy more useful than UV for penicillin compounds?
3. The monobactams contain an SO3 function. How would you establish it has
an N-SO3 and not an O-SO3 or C-SO3 bond?
4. What are the ways to identify the sulfur atom in a molecule?
FURTHER READING
A. G. Brown. 1987. Discovery and development of new β- lactam antibiotics. Pure Appl Chem
59(3):475-484.
K. Schugerl. 2005. Extraction of primary and secondary metabolites. Adv Biochem Eng
Biotechnol 92:1-48.
G. H. Wagman. 1989. Natural Products Isolation: Separation Methods for Antimicrobials,
Antivirals and Enzyme Inhibitors . Elsevier Science Limited.
p eniCillinS
P. Y. Bi, H. R. Dong, and Q. Z. Guo. 2009. Separation and purification of penicillin G from
fermentation broth by solvent sublation. Separation and Purification Technology
65(2):228-231.
P.-Y. Bi, D.-Q. Li, and H.-R. Dong. 2009. A novel technique for the separation and concentra-
tion of penicillin G from fermentation broth: Aqueous two-phase flotation. Separation
and Purification Technology 69(2):205-209.
Q. Liu, J. Yu, W. Li, X. Hu, H. Xia, H. Liu, and P. Yang. 2006. Partitioning behavior of penicil-
lin G in aqueous two phase system formed by ionic liquids and phosphate. Separation
Sci Tech 41(12):2849-2858.
Y. Lu and X. Zhu. 2001. Solvent sublation: Theory and application. Separation Purification
Rev 30(2):157-189.
C ephaloSporinS
B. Neto Ade, M. C. Bustamante, J. H. Oliveira, A. C. Granato, C. Bellao, A. C. Badino,
M. Barboza, and C. O. Hokka. 2012. Preliminary studies for cephamycin C purification
technique. Appl Biochem Biotechnol 166(1):208-221.
C. P. Pang, R. L. White, E. P. Abraham, D. H. Crout, M. Lutstorf, P. J. Morgan, and A. E.
Derome. 1984. Stereochemistry of the incorporation of valine methyl groups into meth-
ylene groups in cephalosporin C. Biochem J 222(3):777-788.