8190. Rhodomycins

Description and references

Antibiotic substance produced by Streptomyces purpurascens nov. sp.: Brockmann, Bauer, Naturwissenschaften 37, 492 (1950); Brockmann et al., Ber. 84, 700 (1951); GB 708749 (1954 to Bayer). Separation of rhodomycin A and rhodomycin B: Brockmann, Patt, Ber. 88, 1455 (1955). Isoln and structural elucidation of additional rhodomycins produced by Streptomyces stammes: Biedermann, Brauniger, Pharmazie 27, 782 (1972); Brockmann et al., Tetrahedron Lett. 1973, 3699. Total synthesis of racemic rhodomycinones (the aglycones of the rhodomycins): A. S. Kende, Y.-G. Tsay, Chem. Commun. 1977, 140.

Chemical structure

Derivative

Rhodomycin A.

Nomenclature

CAS number: 23666-50-4
[7R-(7α,8β,10β)]-8-Ethyl-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-7,10-bis[[2,3,6-trideoxy-3-(dimethylamino)-α-l-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione; β-rhodomycin II.
C36H48N2O12; mol wt 700.77.
C 61.70%, H 6.90%, N 4.00%, O 27.40%.

Description and references

Dec on mild acidic hydrolysis into 1 mole β-rhodomycinone and 2 moles rhodosamine: Brockmann, Spohler, Naturwissenschaften 48, 716 (1961). Structure of β-rhodomycinone: Brockmann, Niemeyer, ibid. 570. Structure of rhodosamine: Brockmann, Spohler, ibid. 42, 154 (1955). Total structure: Brockmann et al., Tetrahedron Lett. 1969, 415.

Derivative

Dihydrochloride.
C36H48N2O12.2HCl; mol wt 773.69.
C 55.89%, H 6.51%, N 3.62%, O 24.82%, Cl 9.16%.

Properties

Red prisms from ethanol + isopropanol, mp 205°. Freely sol in water, lower alcohols; sparingly sol in benzene, chloroform; practically insol in ether, petr ether.

Derivative

Perchlorate.
C36H48N2O12.2HClO4; mol wt 901.69.
C 47.95%, H 5.59%, N 3.11%, O 35.49%, Cl 7.86%.

Properties

Minute red needles, mp 188°. Freely sol in methanol, acetone; sparingly sol in water, butanol.

Derivative

Rhodomycin B.

Nomenclature

CAS number: 1404-52-0
[7R-(7α,8β,10β)]-8-Ethyl-7,8,9,10-tetrahydro-1,6,7,8,11-pentahydroxy-10-[[2,3,6-trideoxy-3-(dimethylamino)-α-l-lyxo-hexopyranosyl]oxy]-5,12-naphthacenedione.
C28H31NO9; mol wt 525.55.
C 63.99%, H 5.95%, N 2.67%, O 27.40%.

Description and references

Dec on mild acidic hydrolysis into 1 mole β-rhodomycinone and 1 mole rhodosamine: Brockmann, Spohler, ibid. 48, 716 (1961).

Derivative

Hydrochloride.

Properties

Red prisms, mp 180°. Freely sol in lower alcohols; sparingly sol in water, acetone. Practically insol in chloroform, benzene.