Kendomycin

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

Hodoodo CAT#: H540256

CAS#: 183202-73-5

Description: Kendomycin is an endothelin receptor antagonist and proteasome inhibitor. It induces apoptosis in lymphoma.


Chemical Structure

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Kendomycin
CAS# 183202-73-5

Theoretical Analysis

Hodoodo Cat#: H540256
Name: Kendomycin
CAS#: 183202-73-5
Chemical Formula: C29H42O6
Exact Mass: 486.30
Molecular Weight: 486.640
Elemental Analysis: C, 71.57; H, 8.70; O, 19.73

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 @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Kendomycin; TAN 2162; TAN-2162; TAN2162

IUPAC/Chemical Name: N/A

InChi Key: HKLDUJXJTQJSEJ-XNTDXEJSSA-N

InChi Code: InChI=1S/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+

SMILES Code: CC1CCC2C(C)C(O)C(C)C(C3=C(O)C(C(C)=C4C3=CC(C(C)CC(C)C/C(C)=C/1)(O)O4)=O)O2

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: >2 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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 486.64 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Tanaka K, Matsuyama H, Watanabe M, Fujimori Y, Ishibashi K, Ozawa T, Sato T, Saikawa Y, Nakata M. Synthesis and biological evaluation of kendomycin and its analogues. J Org Chem. 2014 Nov 7;79(21):9922-47. doi: 10.1021/jo5015273. Epub 2014 Aug 26. PubMed PMID: 25136928.

2: Sengoku T, Xu S, Ogura K, Emori Y, Kitada K, Uemura D, Arimoto H. Total synthesis of the antibiotic kendomycin: a macrocyclization using the Tsuji-Trost etherification. Angew Chem Int Ed Engl. 2014 Apr 14;53(16):4213-6. doi: 10.1002/anie.201400305. Epub 2014 Mar 12. PubMed PMID: 24623596.

3: Elnakady YA, Chatterjee I, Bischoff M, Rohde M, Josten M, Sahl HG, Herrmann M, Müller R. Investigations to the Antibacterial Mechanism of Action of Kendomycin. PLoS One. 2016 Jan 21;11(1):e0146165. doi: 10.1371/journal.pone.0146165. eCollection 2016. PubMed PMID: 26795276; PubMed Central PMCID: PMC4721675.

4: Beck P, Heinemeyer W, Späth AL, Elnakady Y, Müller R, Groll M. Interactions of the natural product kendomycin and the 20S proteasome. J Mol Biol. 2014 Sep 9;426(18):3108-17. doi: 10.1016/j.jmb.2014.06.019. Epub 2014 Jul 16. PubMed PMID: 25038530.

5: Hoffmeister L, Persich P, Fürstner A. Formal total synthesis of kendomycin by way of alkyne metathesis/gold catalysis. Chemistry. 2014 Apr 7;20(15):4396-402. doi: 10.1002/chem.201304580. Epub 2014 Mar 3. PubMed PMID: 24591211.

6: Elnakady YA, Rohde M, Sasse F, Backes C, Keller A, Lenhof HP, Weissman KJ, Müller R. Evidence for the mode of action of the highly cytotoxic Streptomyces polyketide kendomycin. Chembiochem. 2007 Jul 23;8(11):1261-72. PubMed PMID: 17592829.

7: Tanaka K, Watanabe M, Ishibashi K, Matsuyama H, Saikawa Y, Nakata M. Total synthesis of kendomycin featuring intramolecular Dötz benzannulation. Org Lett. 2010 Apr 16;12(8):1700-3. doi: 10.1021/ol100229f. PubMed PMID: 20225835.

8: Xu S, Arimoto H. Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin. J Antibiot (Tokyo). 2016 Apr;69(4):203-12. doi: 10.1038/ja.2016.5. Epub 2016 Feb 10. Review. PubMed PMID: 26860467.

9: Bahnck KB, Rychnovsky SD. Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle. J Am Chem Soc. 2008 Oct 1;130(39):13177-81. doi: 10.1021/ja805187p. Epub 2008 Sep 4. PubMed PMID: 18767844; PubMed Central PMCID: PMC2697922.

10: Martin HJ, Magauer T, Mulzer J. In pursuit of a competitive target: total synthesis of the antibiotic kendomycin. Angew Chem Int Ed Engl. 2010 Aug 2;49(33):5614-26. doi: 10.1002/anie.201000227. Review. PubMed PMID: 20818753.

11: Pichlmair S, Marques MM, Green MP, Martin HJ, Mulzer J. A novel approach toward the synthesis of kendomycin: selective synthesis of a C-aryl glycoside as a single atropisomer. Org Lett. 2003 Nov 27;5(24):4657-9. PubMed PMID: 14627408.

12: Green MP, Pichlmair S, Marques MM, Martin HJ, Diwald O, Berger T, Mulzer J. Synthesis of analogue structures of the p-quinone methide moiety of kendomycin. Org Lett. 2004 Sep 2;6(18):3131-4. PubMed PMID: 15330605.

13: Janssen CO, Lim S, Lo EP, Wan KF, Yu VC, Lee MA, Ng SB, Everett MJ, Buss AD, Lane DP, Boyce RS. Interaction of kendomycin and semi-synthetic analogues with the anti-apoptotic protein Bcl-xl. Bioorg Med Chem Lett. 2008 Nov 1;18(21):5771-3. doi: 10.1016/j.bmcl.2008.09.071. Epub 2008 Sep 23. PubMed PMID: 18845435.

14: Wenzel SC, Bode HB, Kochems I, Müller R. A type I/type III polyketide synthase hybrid biosynthetic pathway for the structurally unique ansa compound kendomycin. Chembiochem. 2008 Nov 3;9(16):2711-21. doi: 10.1002/cbic.200800456. PubMed PMID: 18972512.

15: Williams DR, Shamim K. Efforts toward the total synthesis of (-)-kendomycin. Org Lett. 2005 Sep 15;7(19):4161-4. PubMed PMID: 16146377.

16: Magauer T, Martin HJ, Mulzer J. Total synthesis of the antibiotic kendomycin by macrocyclization using photo-Fries rearrangement and ring-closing metathesis. Angew Chem Int Ed Engl. 2009;48(33):6032-6. doi: 10.1002/anie.200900522. PubMed PMID: 19350596.

17: Lowe JT, Panek JS. Total synthesis of (-)-kendomycin. Org Lett. 2008 Sep 4;10(17):3813-6. doi: 10.1021/ol801499s. Epub 2008 Aug 13. PubMed PMID: 18698784.

18: Smith AB 3rd, Mesaros EF, Meyer EA. Total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis synthetic strategy. J Am Chem Soc. 2005 May 18;127(19):6948-9. PubMed PMID: 15884927.

19: Yuan Y, Men H, Lee C. Total synthesis of kendomycin: a macro-C-glycosidation approach. J Am Chem Soc. 2004 Nov 17;126(45):14720-1. PubMed PMID: 15535687; PubMed Central PMCID: PMC1785127.

20: Mulzer J, Pichlmair S, Green MP, Marques MM, Martin HJ. Toward the synthesis of the carbacylic ansa antibiotic kendomycin. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):11980-5. Epub 2004 Jul 26. PubMed PMID: 15277689; PubMed Central PMCID: PMC514420.