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.


Chemical Structure

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Landomycin A
CAS# 130432-93-8

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

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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

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).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 1087.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.