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Pradimicin T1

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Category Antibiotics
Catalog number BBF-02057
CAS 149598-64-1
Molecular Weight 931.80
Molecular Formula C42H45NO23

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Pradimicin T1 is an antibiotic produced by Actinomyces AA 3798. It has activity against filamentous fungi and yeast-like fungi.

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Synonyms Glycine, N-((5-((6-deoxy-3-O-beta-D-xylopyranosyl-beta-D-galactopyranosyl)oxy)-5,6,8,13-tetrahydro-1,6,9,14-tetrahydroxy-3-methyl-8,13-dioxo-11-(beta-L-xylopyranosyloxy)benzo(a)naphthacen-2-yl)carbonyl)-, (5S-trans)-
IUPAC Name 2-[[(5S,6S)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-1,6,9,14-tetrahydroxy-3-methyl-8,13-dioxo-11-[(2R,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-5,6-dihydrobenzo[a]tetracene-2-carbonyl]amino]acetic acid
Canonical SMILES CC1C(C(C(C(O1)OC2C(C3=CC4=C(C(=C3C5=C2C=C(C(=C5O)C(=O)NCC(=O)O)C)O)C(=O)C6=C(C4=O)C(=CC(=C6)OC7C(C(C(CO7)O)O)O)O)O)O)OC8C(C(C(CO8)O)O)O)O
InChI InChI=1S/C42H45NO23/c1-10-3-16-24(32(55)21(10)39(60)43-7-20(47)48)23-14(29(52)37(16)65-42-36(59)38(26(49)11(2)63-42)66-41-35(58)31(54)19(46)9-62-41)6-15-25(33(23)56)28(51)13-4-12(5-17(44)22(13)27(15)50)64-40-34(57)30(53)18(45)8-61-40/h3-6,11,18-19,26,29-31,34-38,40-42,44-46,49,52-59H,7-9H2,1-2H3,(H,43,60)(H,47,48)/t11-,18+,19-,26+,29+,30-,31+,34+,35-,36-,37+,38+,40-,41+,42+/m1/s1
InChI Key GVEWVQWSVLNZPE-BSAXXBFRSA-N
Appearance Dark Red Amorphous Solid
Antibiotic Activity Spectrum fungi
Boiling Point 1272.9±65.0°C at 760 mmHg
Melting Point 190-195°C (dec.)
Density 1.9±0.1 g/cm3
1. Synthesis and antifungal activity of pradimicin derivatives. Modifications on the aglycone part
S Aburaki, S Okuyama, H Hoshi, H Kamachi, M Nishio, T Hasegawa, S Masuyoshi, S Iimura, M Konishi, T Oki J Antibiot (Tokyo). 1993 Sep;46(9):1447-57. doi: 10.7164/antibiotics.46.1447.
Synthesis and antifungal activity of pradimicin analogs modified on the aglycone part is described. Upon modification studies at various sites of the aglycone part using pradimicin A (PRM A), C-11 position was found to be the sole site to be modified without loosing antifungal activity. Further modification studies at C-11 position were carried out with 11-OH derivative of pradimicin T1 (PRM T1) because of its easy availability. Among the compounds prepared, 11-demethoxy derivative of PRM A (12) and 11-O-ethyl (13) and 11-O-fluoroethyl (14) derivatives of PRM T1 showed promising antifungal activity comparable to that of PRM A.
2. Pradimicins T1 and T2, new antifungal antibiotics produced by an actinomycete. II. Structures and biosynthesis
T Hasegawa, M Kakushima, M Hatori, S Aburaki, S Kakinuma, T Furumai, T Oki J Antibiot (Tokyo). 1993 Apr;46(4):598-605. doi: 10.7164/antibiotics.46.598.
Pradimicins T1 and T2 are new members of the pradimicin family of antibiotics produced by an actinomycete strain AA3798. Pradimicins T1 and T2 are dihydrobenzo[a]naphthacenequinones substituted with 3 and 2 sugar moieties, respectively. The salient feature in their structures is an L-xylose attached to the phenolic hydroxyl group at C-11. Bioconversion experiments using a blocked mutant B-54 of strain AA3798 not only explored a plausible biosynthetic pathway of pradimicins T1 and T2, but also provided evidence of 5S,6S configuration.
3. Pradimicins T1 and T2, new antifungal antibiotics produced by an actinomycete. I. Taxonomy, production, isolation, physico-chemical and biological properties
T Furumai, T Hasegawa, M Kakushima, K Suzuki, H Yamamoto, S Yamamoto, M Hirano, T Oki J Antibiot (Tokyo). 1993 Apr;46(4):589-97. doi: 10.7164/antibiotics.46.589.
Pradimicins T1 and T2, new members of the pradimicin family of antibiotics, were produced by an actinomycete strain AA3798. Pradimicin T1 exhibited potent activity against a wide spectrum of fungi in vitro and demonstrated efficacy against systemic Candida albicans and Aspergillus fumigatus infections in mice.

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