Saquayamycin

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

MedKoo CAT#: 461794

CAS#: 99260-65-8

Description: Saquayamycin is an "aquayamycin-type" antibiotic isolated from Streptomyces nodosus.

Chemical Structure

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Saquayamycin
CAS# 99260-65-8
Instruction

Theoretical Analysis

MedKoo Cat#: 461794
Name: Saquayamycin
CAS#: 99260-65-8
Chemical Formula: C43H48O16
Exact Mass: 820.29
Molecular Weight: 820.840
Elemental Analysis: C, 62.92; H, 5.89; O, 31.19

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: Saquayamycin; Saquayamycin A;

IUPAC/Chemical Name: (3R,4aR,12bS)-4a,8,12b-trihydroxy-9-((2R,4R,5S,6R)-4-hydroxy-6-methyl-5-(((2R,6S)-6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)-3-methyl-3-(((2S,5S,6S)-6-methyl-5-((6-methyl-5-oxo-5,6-dihydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4,4a,12b-tetrahydrotetraphene-1,7,12(2H)-trione

InChi Key: PSCPFFPJZFSAMI-LDNAYASQSA-N

InChi Code: InChI=1S/C43H48O16/c1-19-26(44)8-11-32(54-19)57-29-10-13-34(56-21(29)3)59-41(5)17-31(47)43(52)36-25(14-15-42(43,51)18-41)38(49)35-24(39(36)50)7-6-23(37(35)48)30-16-28(46)40(22(4)53-30)58-33-12-9-27(45)20(2)55-33/h6-9,11-12,14-15,19-22,28-30,32-34,40,46,48,51-52H,10,13,16-18H2,1-5H3/t19?,20-,21-,22+,28+,29-,30+,32?,33-,34-,40+,41-,42-,43-/m0/s1

SMILES Code: O=C1C[C@](C)(O[C@H]2CC[C@H](OC3C=CC(C(C)O3)=O)[C@H](C)O2)C[C@]4(O)[C@@]1(O)C5=C(C(C6=C(C5=O)C=CC([C@H]7C[C@H]([C@@H]([C@@H](C)O7)O[C@H]8C=CC([C@H](C)O8)=O)O)=C6O)=O)C=C4

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 820.84 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: Antal N, Fiedler HP, Stackebrandt E, Beil W, Ströch K, Zeeck A. Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tü 6368. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot (Tokyo). 2005 Feb;58(2):95-102. PubMed PMID: 15835721.

2: Ströch K, Zeeck A, Antal N, Fiedler HP. Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp. Tü 6368. II. Structure elucidation. J Antibiot (Tokyo). 2005 Feb;58(2):103-10. PubMed PMID: 15835722.

3: Erb A, Luzhetskyy A, Hardter U, Bechthold A. Cloning and sequencing of the biosynthetic gene cluster for saquayamycin Z and galtamycin B and the elucidation of the assembly of their saccharide chains. Chembiochem. 2009 May 25;10(8):1392-401. doi: 10.1002/cbic.200900054. PubMed PMID: 19384899.

4: Shaaban KA, Ahmed TA, Leggas M, Rohr J. Saquayamycins G-K, cytotoxic angucyclines from Streptomyces sp. Including two analogues bearing the aminosugar rednose. J Nat Prod. 2012 Jul 27;75(7):1383-92. doi: 10.1021/np300316b. Epub 2012 Jul 3. PubMed PMID: 22758660; PubMed Central PMCID: PMC3412564.

5: Aouiche A, Bijani C, Zitouni A, Mathieu F, Sabaou N. Antimicrobial activity of saquayamycins produced by Streptomyces spp. PAL114 isolated from a Saharan soil. J Mycol Med. 2014 Jun;24(2):e17-23. doi: 10.1016/j.mycmed.2013.09.001. Epub 2013 Oct 16. PubMed PMID: 24139182.

6: Nakagawa K, Hara C, Tokuyama S, Takada K, Imamura N. Saprolmycins A-E, new angucycline antibiotics active against Saprolegnia parasitica. J Antibiot (Tokyo). 2012 Dec;65(12):599-607. doi: 10.1038/ja.2012.86. Epub 2012 Oct 24. PubMed PMID: 23093030.

7: Rozek T, Bowie JH, Skelton BW, White AH. 11-Hydroxy-3,3-dimethyl-7,12-dioxo-3,4,6,6a,7,12,12a,12b-octahydrobenz[a]anthrace n-1-yl acetate. Acta Crystallogr C. 2003 Aug;59(Pt 8):o431-2. Epub 2003 Jul 12. PubMed PMID: 12909769.

8: Alvi KA, Baker DD, Stienecker V, Hosken M, Nair BG. Identification of inhibitors of inducible nitric oxide synthase from microbial extracts. J Antibiot (Tokyo). 2000 May;53(5):496-501. PubMed PMID: 10908113.

9: Uchida T, Imoto M, Watanabe Y, Miura K, Dobashi T, Matsuda N, Sawa T, Naganawa H, Hamada M, Takeuchi T. Saquayamycins, new aquayamycin-group antibiotics. J Antibiot (Tokyo). 1985 Sep;38(9):1171-81. PubMed PMID: 3840796.

10: Abdelfattah MS, Kharel MK, Hitron JA, Baig I, Rohr J. Moromycins A and B, isolation and structure elucidation of C-glycosylangucycline-type antibiotics from Streptomyces sp. KY002. J Nat Prod. 2008 Sep;71(9):1569-73. doi: 10.1021/np800281f. Epub 2008 Jul 31. PubMed PMID: 18666798; PubMed Central PMCID: PMC2562265.

11: Sekizawa R, Iinuma H, Naganawa H, Hamada M, Takeuchi T, Yamaizumi J, Umezawa K. Isolation of novel saquayamycins as inhibitors of farnesyl-protein transferase. J Antibiot (Tokyo). 1996 May;49(5):487-90. PubMed PMID: 8682727.

12: Salem SM, Weidenbach S, Rohr J. Two Cooperative Glycosyltransferases Are Responsible for the Sugar Diversity of Saquayamycins Isolated from Streptomyces sp. KY 40-1. ACS Chem Biol. 2017 Oct 20;12(10):2529-2534. doi: 10.1021/acschembio.7b00453. Epub 2017 Sep 13. PubMed PMID: 28892347; PubMed Central PMCID: PMC5886728.