Landomycin A

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598282

CAS#: 130432-93-8

Description: Landomycin A is a prominent angucycline hexasaccharide antibiotic isolated from Streptomyces sp.


Price and Availability

Size
Price

Size
Price

Size
Price

Landomycin A is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 598282
Name: Landomycin A
CAS#: 130432-93-8
Chemical Formula: C55H74O22
Exact Mass: 1086.4672
Molecular Weight: 1087.17
Elemental Analysis: C, 60.76; H, 6.86; O, 32.38


Synonym: Landomycin A;

IUPAC/Chemical Name: (R)-1,6,11-trihydroxy-8-(((2S,4R,5S,6R)-4-hydroxy-5-(((2R,3S,5R,6S)-5-hydroxy-3-(((2R,5R,6S)-5-(((2R,4S,5R,6S)-4-hydroxy-5-(((2S,4R,5S,6S)-5-hydroxy-4-(((2R,5S,6S)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3-methyl-5,6-dihydrotetraphene-7,12-dione

InChi Key: PULJTZNQAHCUDQ-BLHMSWSRSA-N

InChi Code: InChI=1S/C55H74O22/c1-21-14-28-16-33(60)47-49(45(28)32(59)15-21)52(65)46-30(57)8-10-37(48(46)51(47)64)73-43-19-35(62)54(27(7)70-43)77-55-39(17-31(58)23(3)71-55)75-41-13-11-36(24(4)67-41)72-42-18-34(61)53(26(6)69-42)76-44-20-38(50(63)25(5)68-44)74-40-12-9-29(56)22(2)66-40/h8,10,14-15,22-27,29,31,33-36,38-44,50,53-63H,9,11-13,16-20H2,1-7H3/t22-,23-,24-,25-,26-,27+,29-,31+,33+,34-,35+,36+,38+,39-,40+,41+,42+,43-,44-,50-,53-,54+,55+/m0/s1

SMILES Code: C[C@@H]([C@H](O)[C@H](O[C@@H]1CC[C@H](O)[C@H](C)O1)C2)O[C@H]2O[C@@H]([C@H](C)O3)[C@@H](O)C[C@H]3O[C@@H]([C@H](C)O4)CC[C@H]4O[C@@H](C[C@H]([C@H](C)O5)O)[C@H]5O[C@@H]([C@H](O)C6)[C@@H](C)O[C@H]6Oc7ccc(O)c(C(C8=C9[C@H](O)Cc%10cc(C)cc(O)c%108)=O)c7C9=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.03.00


References

1: Yang X, Wang P, Yu B. Tackling the challenges in the total synthesis of landomycin A. Chem Rec. 2013 Feb;13(1):70-84. doi: 10.1002/tcr.201200018. Epub 2013 Feb 6. PubMed PMID: 23389835.

2: Baryal KN, Zhu J. Stereoselective Synthesis of S-Linked Hexasaccharide of Landomycin A via Umpolung S-Glycosylation. Org Lett. 2015 Sep 18;17(18):4530-3. doi: 10.1021/acs.orglett.5b02223. Epub 2015 Sep 3. PubMed PMID: 26334208.

3: Myronovskyi M, Brötz E, Rosenkränzer B, Manderscheid N, Tokovenko B, Rebets Y, Luzhetskyy A. Generation of new compounds through unbalanced transcription of landomycin A cluster. Appl Microbiol Biotechnol. 2016 Nov;100(21):9175-9186. Epub 2016 Jul 13. PubMed PMID: 27412461.

4: Yang X, Fu B, Yu B. Total synthesis of landomycin A, a potent antitumor angucycline antibiotic. J Am Chem Soc. 2011 Aug 17;133(32):12433-5. doi: 10.1021/ja205339p. Epub 2011 Jul 27. PubMed PMID: 21780843.

5: Lehka LV, Panchuk RR, Berger W, Rohr J, Stoika RS. THE ROLE OF REACTIVE OXYGEN SPECIES IN TUMOR CELLS APOPTOSIS INDUCED BY LANDOMYCIN A. Ukr Biochem J. 2015 Sep-Oct;87(5):72-82. PubMed PMID: 26717598.

6: Luzhetskyy A, Liu T, Fedoryshyn M, Ostash B, Fedorenko V, Rohr J, Bechthold A. Function of lanGT3, a glycosyltransferase gene involved in landomycin A biosynthesis. Chembiochem. 2004 Nov 5;5(11):1567-70. PubMed PMID: 15515090.

7: Mayer A, Taguchi T, Linnenbrink A, Hofmann C, Luzhetskyy A, Bechthold A. LanV, a bifunctional enzyme: aromatase and ketoreductase during landomycin A biosynthesis. Chembiochem. 2005 Dec;6(12):2312-5. PubMed PMID: 16283688.

8: von Mulert U, Luzhetskyy A, Hofmann C, Mayer A, Bechthold A. Expression of the landomycin biosynthetic gene cluster in a PKS mutant of Streptomyces fradiae is dependent on the coexpression of a putative transcriptional activator gene. FEMS Microbiol Lett. 2004 Jan 15;230(1):91-7. PubMed PMID: 14734170.

9: Luzhetskyy A, Taguchi T, Fedoryshyn M, Dürr C, Wohlert SE, Novikov V, Bechthold A. LanGT2 Catalyzes the First Glycosylation Step during landomycin A biosynthesis. Chembiochem. 2005 Aug;6(8):1406-10. PubMed PMID: 15977274.

10: Tanaka H, Yamaguchi S, Yoshizawa A, Takagi M, Shin-ya K, Takahashi T. Combinatorial synthesis of deoxyhexasaccharides related to the landomycin A sugar moiety, based on an orthogonal deprotection strategy. Chem Asian J. 2010 Jun 1;5(6):1407-24. doi: 10.1002/asia.200900640. PubMed PMID: 20480491.

11: Luzhetskyy A, Fedoryshyn M, Dürr C, Taguchi T, Novikov V, Bechthold A. Iteratively acting glycosyltransferases involved in the hexasaccharide biosynthesis of landomycin A. Chem Biol. 2005 Jul;12(7):725-9. PubMed PMID: 16039521.

12: Erb A, Krauth C, Luzhetskyy A, Bechthold A. Differences in the substrate specificity of glycosyltransferases involved in landomycins A and E biosynthesis. Appl Microbiol Biotechnol. 2009 Jul;83(6):1067-76. doi: 10.1007/s00253-009-1993-9. Epub 2009 Apr 8. PubMed PMID: 19352642.

13: Crow RT, Rosenbaum B, Smith R 3rd, Guo Y, Ramos KS, Sulikowski GA. Landomycin A inhibits DNA synthesis and G1/S cell cycle progression. Bioorg Med Chem Lett. 1999 Jun 21;9(12):1663-6. PubMed PMID: 10397496.

14: Rebets Y, Dutko L, Ostash B, Luzhetskyy A, Kulachkovskyy O, Yamaguchi T, Nakamura T, Bechthold A, Fedorenko V. Function of lanI in regulation of landomycin A biosynthesis in Streptomyces cyanogenus S136 and cross-complementation studies with Streptomyces antibiotic regulatory proteins encoding genes. Arch Microbiol. 2008 Feb;189(2):111-20. Epub 2007 Sep 5. PubMed PMID: 17786405.

15: Kharel MK, Pahari P, Shaaban KA, Wang G, Morris C, Rohr J. Elucidation of post-PKS tailoring steps involved in landomycin biosynthesis. Org Biomol Chem. 2012 Jun 7;10(21):4256-65. doi: 10.1039/c2ob07171a. Epub 2012 Mar 27. PubMed PMID: 22454092.

16: Zhu L, Luzhetskyy A, Luzhetska M, Mattingly C, Adams V, Bechthold A, Rohr J. Generation of new landomycins with altered saccharide patterns through over-expression of the glycosyltransferase gene lanGT3 in the biosynthetic gene cluster of landomycin A in Streptomyces cyanogenus S-136. Chembiochem. 2007 Jan 2;8(1):83-8. PubMed PMID: 17139690; PubMed Central PMCID: PMC2879348.

17: Yu B, Wang P. Efficient synthesis of the hexasaccharide fragment of landomycin A: using phenyl 2,3-O-thionocarbonyl-1-thioglycosides as 2-deoxy-beta-glycoside precursors. Org Lett. 2002 May 30;4(11):1919-22. PubMed PMID: 12027647.

18: Roush WR, Neitz RJ. Studies on the synthesis of landomycin A. Synthesis of the originally assigned structure of the aglycone, landomycinone, and revision of structure. J Org Chem. 2004 Jul 23;69(15):4906-12. PubMed PMID: 15255715.

19: Roush WR, Bennett CE, Roberts SE. Studies on the synthesis of landomycin A: synthesis and glycosidation reactions of L-rhodinosyl acetate derivatives. J Org Chem. 2001 Sep 21;66(19):6389-93. PubMed PMID: 11559191.

20: Westrich L, Domann S, Faust B, Bedford D, Hopwood DA, Bechthold A. Cloning and characterization of a gene cluster from Streptomyces cyanogenus S136 probably involved in landomycin biosynthesis. FEMS Microbiol Lett. 1999 Jan 15;170(2):381-7. PubMed PMID: 9933932.