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MedKoo Cat#: 584572 | Name: Mycarose

Description:

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

Mycarose is a sugar epi-axenose to lyxo configeration.

Chemical Structure

Mycarose
Mycarose
CAS#6032-92-4

Theoretical Analysis

MedKoo Cat#: 584572

Name: Mycarose

CAS#: 6032-92-4

Chemical Formula: C7H14O4

Exact Mass: 162.0892

Molecular Weight: 162.19

Elemental Analysis: C, 51.84; H, 8.70; O, 39.46

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Mycarose; 3-Epi-axenose
IUPAC/Chemical Name
2,6-Dideoxy-3-C-methyl-lyxo-hexose
InChi Key
JYAQWANEOPJVEY-LYFYHCNISA-N
InChi Code
InChI=1S/C7H14O4/c1-5(9)6(10)7(2,11)3-4-8/h4-6,9-11H,3H2,1-2H3/t5-,6-,7+/m0/s1
SMILES Code
O=CC[C@@]([C@H]([C@H](C)O)O)(C)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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 162.19 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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A two-stage one-pot enzymatic synthesis of TDP-L-mycarose from thymidine and glucose-1-phosphate. J Am Chem Soc. 2006 Feb 8;128(5):1432-3. PubMed PMID: 16448097; PubMed Central PMCID: PMC2502060. 6: Peirú S, Rodríguez E, Tran CQ, Carney JR, Gramajo H. Characterization of the heterodimeric MegBIIa:MegBIIb aldo-keto reductase involved in the biosynthesis of L-mycarose from Micromonospora megalomicea. Biochemistry. 2007 Jul 10;46(27):8100-9. Epub 2007 Jun 16. PubMed PMID: 17571859. 7: Poulsen SM, Kofoed C, Vester B. Inhibition of the ribosomal peptidyl transferase reaction by the mycarose moiety of the antibiotics carbomycin, spiramycin and tylosin. J Mol Biol. 2000 Dec 1;304(3):471-81. PubMed PMID: 11090288. 8: WATANABE T, FUJII T, SATAKE K. 4-O-Acetyl mycarose. A new O-acetyl sugar obtained from leucomycin minor components. J Biochem. 1961 Sep;50:197-201. PubMed PMID: 14005205. 9: González A, Remsing LL, Lombó F, Fernández MJ, Prado L, Braña AF, Künzel E, Rohr J, Méndez C, Salas JA. The mtmVUC genes of the mithramycin gene cluster in Streptomyces argillaceus are involved in the biosynthesis of the sugar moieties. Mol Gen Genet. 2001 Feb;264(6):827-35. PubMed PMID: 11254130. 10: Zhao Z, Jin L, Xu Y, Zhu D, Liu Y, Liu C, Lei P. Synthesis and antibacterial activity of a series of novel 9-O-acetyl- 4'-substituted 16-membered macrolides derived from josamycin. Bioorg Med Chem Lett. 2014 Jan 15;24(2):480-4. doi: 10.1016/j.bmcl.2013.12.029. Epub 2013 Dec 15. PubMed PMID: 24374276. 11: Salah-Bey K, Doumith M, Michel JM, Haydock S, Cortés J, Leadlay PF, Raynal MC. Targeted gene inactivation for the elucidation of deoxysugar biosynthesis in the erythromycin producer Saccharopolyspora erythraea. Mol Gen Genet. 1998 Mar;257(5):542-53. PubMed PMID: 9563840. 12: Haupt I, Fricke H, Cerná J, Rychlík I. Effect of demycarosylturimycin on ribosomal peptidyltransferase from Escherichia coli. J Antibiot (Tokyo). 1978 Jun;31(6):610-5. PubMed PMID: 355215. 13: Remsing LL, Garcia-Bernardo J, Gonzalez A, Künzel E, Rix U, Braña AF, Bearden DW, Méndez C, Salas JA, Rohr J. Ketopremithramycins and ketomithramycins, four new aureolic acid-type compounds obtained upon inactivation of two genes involved in the biosynthesis of the deoxysugar moieties of the antitumor drug mithramycin by Streptomyces argillaceus, reveal novel insights into post-PKS tailoring steps of the mithramycin biosynthetic pathway. J Am Chem Soc. 2002 Feb 27;124(8):1606-14. PubMed PMID: 11853433; PubMed Central PMCID: PMC4480631. 14: Epp JK, Huber ML, Turner JR, Goodson T, Schoner BE. Production of a hybrid macrolide antibiotic in Streptomyces ambofaciens and Streptomyces lividans by introduction of a cloned carbomycin biosynthetic gene from Streptomyces thermotolerans. Gene. 1989 Dec 28;85(2):293-301. PubMed PMID: 2628170. 15: Peirú S, Menzella HG, Rodríguez E, Carney J, Gramajo H. Production of the potent antibacterial polyketide erythromycin C in Escherichia coli. Appl Environ Microbiol. 2005 May;71(5):2539-47. PubMed PMID: 15870344; PubMed Central PMCID: PMC1087553. 16: Wang Z, Jian T, Phan LT, Or YS. Synthesis of novel 4'-substituted 16-membered ring macrolide antibiotics derived from leucomycins. Bioorg Med Chem Lett. 2004 Jan 19;14(2):519-21. PubMed PMID: 14698194. 17: Reuter G, Hüttner R, Fricke H. [Physiology and biochemistry of streptomycetes. 4. Isolation and identification of mycarose, mycaminose and desmycarosyl-antibiotic from the macrocide-antibiotic a 6599 (Turimycin)]. Pharmazie. 1976;31(1):48-50. German. PubMed PMID: 1257279. 18: Kurihara K, Kikuchi N, Ajito K. Cladinose analogues of sixteen-membered macrolide antibiotics. III. Efficient synthesis of 4-O-alkyl-L-cladinose analogues: improved antibacterial activities compatible with pharmacokinetics. J Antibiot (Tokyo). 1997 Jan;50(1):32-44. PubMed PMID: 9066764. 19: Pérez M, Baig I, Braña AF, Salas JA, Rohr J, Méndez C. Generation of new derivatives of the antitumor antibiotic mithramycin by altering the glycosylation pattern through combinatorial biosynthesis. Chembiochem. 2008 Sep 22;9(14):2295-304. doi: 10.1002/cbic.200800299. PubMed PMID: 18756551; PubMed Central PMCID: PMC2574993. 20: Jiang M, Zhang H, Park SH, Li Y, Pfeifer BA. Deoxysugar pathway interchange for erythromycin analogues heterologously produced through Escherichia coli. Metab Eng. 2013 Nov;20:92-100. doi: 10.1016/j.ymben.2013.09.005. Epub 2013 Sep 20. PubMed PMID: 24060454.