Studies on Tuberactinomycin. Iii

β‐Amino Acid Biosynthesis

“…In Archaea, such as Methanosarcina thermophila, N e -acetylb-lysine serves as an osmolyte [37]. b-Lysine is present as a constituent of several secondary metabolites from bacteria, such as in albothricin (32) [41], capreomycins IA (36) and IB (37) [42], lysinomycin [43], myomycin [44], and tallysomycin A [45].…”

“…In addition, (S)-Dap (67) is a constituent of the bleomycins (Figure 4.14), which are glycopeptide antibiotics isolated from Streptomyces verticillus [101]. It is also present in viomycin (34) [40], tuberactinomycin O (35) [41], and the capreomycins IA (36) and IB (37) [42], tuberculostatic cyclic peptide antibiotics from Streptomyces species that are structurally closely related to each other ( (67) Like (S)-Dap (67), 2,3-Dab (68) can also be found in nature in its free form. For instance, both the (2R,3S) isomer and the (2S,3S) isomer of 2,3-Dab are present in the roots of Lotus tenuis [105].…”

“…In addition, 2,3-Dab (68) serves as a constituent in the aciculitins A (75), B (76), and C (77) (Figure 4.13), bicyclic glycopeptides isolated from the marine sponge Aciculites orientalis [106], in the papuamides A (78) and B (79) (Figure 4.13), cyclic depsipeptides isolated from sponges of the genus Theonella [107], and in quinaldopeptin, a cyclopeptide from Streptoverticillium album Q132-6 [108]. Capreomycidine (69) is a cyclic guanidino amino acid occurring as a constituent of the tuberculostatic capreomycins [42] and the structurally closely related compounds LL-BM547a, LL-BM547b [46], the tuberactinomycins [41], and viomycin (34) [40] ( Figure 4.4), while streptolidine (70) is present in the streptothricins, for instance in streptothricin F (33) [39] (Figure 4.3), broad-spectrum peptidyl nucleoside antibiotics that were isolated from Streptomyces lavendulae.…”

“…Nucleophilic attack from the amino group of asparagine at C-3 of the 2,3-dehydroserine derivative 84 yields the dipeptide 85 (Scheme 4.11) [109]. (Figure 4.4), the capreomycins [42] and the tuberactinomycins [41] belong to the tuberactinomycin family, a class of cyclic pentapeptide antibiotics which are used for the treatment of multidrug-resistant tuberculosis infections. Viomycin (34) and all other related representatives of the tuberactinomycin family contain both a 2,3-Dap (67) and either a capreomycidine (69) or a hydroxylated capreomycidine moiety (Figure 4.4).…”

A biomimetic domino reaction for the concise synthesis of capreomycidine and epicapreomycidine

“…1). Capreomycidine 1 can be found in tuberactinomycin peptide antibiotics (Nagata et al 1968; Wakamiya et al 1970; Yoshioka et al 1971; Ando et al 1971; Izumi et al 1972), e.g ., the capreomycins (Herr et al 1960; Bycroft et al 1971a; Shiba et al 1976; Nomoto et al 1977; Nomoto et al 1978) and viomycin 3 (Finlay et al 1951; Bartz et al 1951; Dyer et al 1965; Bycroft et al 1969; Noda et al 1972), which have both found clinical use as anti-tuberculosis drugs. The 3-epimer epicapreomycidine 2 is a component of the naturally occurring protease inhibitors chymostatin (Umezawa et al 1970; Tatsuta et al 1973) and elastatinal (Umezawa et al 1973; Okura et al 1975) as well as of the Streptomyces -produced muraymycins, a subclass of nucleoside lipopeptide antibiotics (e.g.…”