Sporidesmolides
Title: Sporidesmolides
Literature References: Cyclodepsipeptides containing both D and L amino acids, isolated from the pasture fungus Sporidesmium bakeri Syd. (Pithomyces chartarum (Berk. & Curt.) Ellis): D. W. Russell, Biochim. Biophys. Acta 45, 411 (1960); W. S. Bertaud et al., J. Gen. Microbiol. 32, 385 (1963); E. Bishop, D. W. Russell, Biochem. J. 92, 19P (1964).
 
Derivative Type: Sporidesmolide I
CAS Registry Number: 2900-38-1
Molecular Formula: C33H58N4O8
Molecular Weight: 638.84
Percent Composition: C 62.04%, H 9.15%, N 8.77%, O 20.04%
Literature References: Structure: D. W. Russell, J. Chem. Soc. 1962, 753. Synthesis: M. M. Shemyakin et al., Tetrahedron 19, 995 (1963). Biosynthetic study: D. W. Russell, Biochim. Biophys. Acta 261, 469 (1972). MS determn: B. C. Das et al., J. Antibiot. 32, 569 (1979).
Properties: Needles from 70% acetic acid, mp 261-263°. [a]D17 -217° (c = 1.5 in chloroform). Practically insol in water; very sol in chloroform; sparingly sol in other common organic solvents.
Melting point: mp 261-263°
Optical Rotation: [a]D17 -217° (c = 1.5 in chloroform)
 
Derivative Type: Sporidesmolide II
CAS Registry Number: 3200-75-7
CAS Name: 2-D-Alloisoleucine sporidesmolide I
Molecular Formula: C34H60N4O8
Molecular Weight: 652.86
Percent Composition: C 62.55%, H 9.26%, N 8.58%, O 19.61%
Literature References: Structure and synthesis: M. M. Shemyakin et al., Tetrahedron Lett. 1963, 1927.
Properties: Crystals, mp 228-230°. [a]D20 -195° (c = 0.6 in chloroform).
Melting point: mp 228-230°
Optical Rotation: [a]D20 -195° (c = 0.6 in chloroform)
 
Derivative Type: Sporidesmolide III
CAS Registry Number: 1803-67-4
CAS Name: 6-L-Leucine sporidesmolide I
Molecular Formula: C32H56N4O8
Molecular Weight: 624.81
Percent Composition: C 61.51%, H 9.03%, N 8.97%, O 20.49%
Literature References: Synthesis: Y. A. Ovchinnikov et al., ibid. 1965, 1111.
Properties: Crystals, mp 277-278°. [a]D -80° (c = 1.6 in acetic acid).
Melting point: mp 277-278°
Optical Rotation: [a]D -80° (c = 1.6 in acetic acid)
 
Derivative Type: Sporidesmolide IV
CAS Registry Number: 10252-34-3
CAS Name: 4-(4-Methyl-L-2-hydroxypentanoic acid) sporidesmolide I
Molecular Formula: C34H60N4O8
Molecular Weight: 652.86
Percent Composition: C 62.55%, H 9.26%, N 8.58%, O 19.61%
Literature References: Structure and synthesis: A. A. Kiryushkin et al., ibid. 1965, 143; E. Bishop, D. W. Russell, J. Chem. Soc. C 1967, 634.
Properties: Crystals, mp 227-228°. [a]D -195° (c = 1 in chloroform). Practically insol in water, sol in chloroform, moderately sol in common organic solvents.
Melting point: mp 227-228°
Optical Rotation: [a]D -195° (c = 1 in chloroform)

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