References of 18H-16a,19-Metheno-16aH-benzo[e]naphtho[2,1-m][1,4]dioxacyclopentadecin-14-carboxylicacid, 4-[[4-O-[3-O-(3-chloro-6-methoxy-2-methylbenzoyl)-2,6-dideoxy-b-D-arabino-hexopyranosyl]-2,6-dideoxy-b-D-arabino-hexopyranosyl]oxy]-1,2,3,4,4a,6a,7,8,9,10,12a,15,16,21,21a,21b-hexadecahydro-22-hydroxy-15,21a-dimethyl-18,21-dioxo-,(4S,4aS,6aR,11E,12aR,15R,16aS,21aR,21bR)-
Title: Chlorothricin
CAS Registry Number: 34707-92-1
Molecular Formula: C50H63ClO16
Molecular Weight: 955.48
Percent Composition: C 62.85%, H 6.65%, Cl 3.71%, O 26.79%
Literature References: Macrolide antibiotic active against gram-positive bacteria. Isolated together with its dechloro analog from Tü 99, a strain of
Streptomyces antibioticus: Keller-Schierlein
et al., Helv. Chim. Acta 52, 127 (1969). Degradation products studies: Muntwyler
et al., ibid. 53, 1544 (1970). Structure: Muntwyler, Keller-Schierlein,
ibid. 55, 2071 (1972). Non-competitive inhibitor of pyruvate carboxylase: P. W. Schindler, H. Zaehner,
Arch. Mikrobiol. 82, 66, (1972); P. W. Schindler, M. C. Scrutton,
ibid. 55, 543 (1975). Biosynthetic studies: O. Mascaretti
et al., J. Nat. Prod. 42, 455 (1979);
eidem, Biochemistry 20, 919 (1981). Partial synthesis of the aglycone,
chlorothricolide: R. E. Ireland, W. J. Thompson,
J. Org. Chem. 44, 3041 (1979); R. E. Ireland
et al., ibid. 46, 4863 (1981); W. R. Roush, S. E. Hall,
J. Am. Chem. Soc. 103, 5200 (1981). Alternate synthetic approach: R. E. Ireland, M. D. Varney,
J. Org. Chem. 51, 635 (1986).
Review: Keller-Schierlein,
Fortschr. Chem. Org. Naturst. 30, 394-396 (1973); H. G. Floss, C.-J. Chang,
Antibiotics vol. IV, J. W. Corcoran, Ed. (Springer-Verlag, New York, 1981) pp 193-214.
Properties: Colorless crystals from methylene chloride-methyl acetate, mp 206-207°. uv max (alc): 222, 260 nm (log e 4.20, 3.81); (0.01
N alc KOH): 221, 259 nm (log e 4.09, 3.95). Dibasic acid; pK: 5.01, 7.91. (The above data applies to a 5:1 mixture with dechlorothricin, Muntwyler, Keller-Schierlein,
loc. cit.). Slightly sol in water; readily sol in organic solvents of medium polarity.
Melting point: mp 206-207°
pKa: pK: 5.01, 7.91
Absorption maximum: uv max (alc): 222, 260 nm (log e 4.20, 3.81); (0.01
N alc KOH): 221, 259 nm (log e 4.09, 3.95)
![CAS No:34707-92-1 18H-16a,19-Metheno-16aH-benzo[e]naphtho[2,1-m][1,4]dioxacyclopentadecin-14-carboxylicacid, 4-[[4-O-[3-O-(3-chloro-6-methoxy-2-methylbenzoyl)-2,6-dideoxy-b-D-arabino-hexopyranosyl]-2,6-dideoxy-b-D-arabino-hexopyranosyl]oxy]-1,2,3,4,4a,6a,7,8,9,10,12a,15,16,21,21a,21b-hexadecahydro-22-hydroxy-15,21a-dimethyl-18,21-dioxo-,(4S,4aS,6aR,11E,12aR,15R,16aS,21aR,21bR)-](/structure/cas-347/34707-92-1.png)
