Structure of a protected C3-C10 subunit of erythromycin and its C8 epimer.
(1) (2S,3R,4R,6R)-3,4-O-Carbonyl-7,7-dimethylenedithio-2,4,6-trimet hylnonane-1,3,4-triol, C15H26O4S2, M(r) = 334.49, triclinic, P1, a = 6.460 (2), b = 8.917 (3), c = 15.616 (5) A, alpha = 83.60 (3), beta = 83.41 (2), gamma = 89.52 (2) degrees, V = 888.0 (5) A3, Z = 2, Dx = 1.25 g cm-3, mu = 2.980 cm-1, lambda (Mo K alpha) = 0.7107 A, F(000) = 360, T = 298 K, R = 0.0465 for 1832 reflections [Fo greater than or equal to 4 sigma (Fo)]. (2) (2S,3R,4R,6S)-3,4-O-Carbonyl-7,7-dimethylenedithio-2,4,6-trimet hylnonane-1,3,4-triol, C15H26O4S2, M(r) = 334.49, monoclinic, P21, a = 8.1849 (8), b = 8.9456 (14), c = 12.0258 (14) A, beta = 100.878 (8) degrees, V = 864.7 (2) A3, Z = 2, Dx = 1.28 g cm-3, mu = 3.060 cm-1, lambda (Mo K alpha) = 0.7107 A, F(000) = 360, T = 298 K, R = 0.0569 for 2001 reflections [Fo greater than or equal to 4 sigma (Fo)]. The two diastereomers differ in configuration at C6. For (1) there are two unique molecules in the unit cell. These two molecules differ in conformation by a rotation about the bond C7-C8. The molecules are hydrogen bonded into infinite chains along b. The hydroxyl O atom of molecule (2), O10', acts as both a donor and an acceptor in hydrogen-bonding interactions with the carbonyl O atom, O14, and the hydroxyl H atom, H10, of molecule (1).(ABSTRACT TRUNCATED AT 250 WORDS)
Lynch
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Department of Chemistry and Biochemistry, University of Texas, Austin 78712.
Lee
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Martin
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Davis
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D004917:Erythromycin / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D004917:Erythromycin