2315. Circulins

Description and references

Polypeptide antibiotics related to polymyxins. Produced by Bacillus circulans, a microorganism found in soil and dust: Murray, Tetrault, Proc. Soc. Am. Bact. 1, 20 (1948); McLeod, J. Bacteriol. 56, 749 (1948); Murray et al., ibid. 57, 305 (1949). Isoln yields circulins A and B, circulin A being the major component: Tetrault, US 2676133 (1954 to Purdue Res. Found.). Review: Vogner, Studer, Experientia 22, 345 (1966).

Chemical structure

Derivative

Circulin A.
C53H100N16O13; mol wt 1169.46.
C 54.43%, H 8.62%, N 19.16%, O 17.79%.

Description and references

Structure: Fujikawa et al., Experientia 21, 307 (1965). Synthesis: Studer et al., Helv. Chim. Acta 49, 974 (1966).

Derivative

Sulfate.
C53H100N16O13.2 1/2 H2SO4.

Properties

Crystals or amorphous solid, dec 226-228°. [α]D25 -61.6° (c = 1.25). Sol in water; less sol in the lower alcs. Practically insol in acetone and water-immiscible solvents.

Derivative

Circulin B.
C52H98N16O13; mol wt 1155.43.
C 54.05%, H 8.55%, N 19.40%, O 18.00%.

Description and references

Structure: Hayashi et al., Experientia 24, 656 (1968).