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MedKoo Cat#: 598234 | Name: Laidlomycin

Description:

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

Laidlomycin is a polycyclic, polyether, monocarboxylic acid posessing inhibitory activity against various Mycoplasma species, especially Acholeplasma laidlawii.

Chemical Structure

Laidlomycin
Laidlomycin
CAS#56283-74-0

Theoretical Analysis

MedKoo Cat#: 598234

Name: Laidlomycin

CAS#: 56283-74-0

Chemical Formula: C37H62O12

Exact Mass: 698.4241

Molecular Weight: 698.89

Elemental Analysis: C, 63.59; H, 8.94; O, 27.47

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
Laidlomycin; Laidlomicina; Laidlomycinum;
IUPAC/Chemical Name
(2S,3R,4R)-4-((2S,5R,7S,8R,9S)-9-hydroxy-2-((2S,2'R,3'S,5R,5'R)-5'-((2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl)-2-methyl-3-(propionyloxy)pentanoic acid
InChi Key
ZNBNBTIDJSKEAM-NISBWGIBSA-N
InChi Code
InChI=1S/C37H62O12/c1-10-28(40)45-30(24(7)33(41)42)23(6)31-22(5)25(39)17-36(47-31)14-13-34(8,49-36)27-11-12-35(9,46-27)32-20(3)16-26(44-32)29-19(2)15-21(4)37(43,18-38)48-29/h19-27,29-32,38-39,43H,10-18H2,1-9H3,(H,41,42)/t19-,20-,21+,22+,23-,24-,25-,26+,27+,29-,30+,31-,32+,34-,35-,36+,37-/m0/s1
SMILES Code
CCC(O[C@@H]([C@@H](C(O)=O)C)[C@@H]([C@H]1O[C@]2(C[C@@H]([C@H]1C)O)CC[C@](O2)([C@H]3CC[C@](O3)([C@@H]4O[C@@H]([C@H]5O[C@@](CO)([C@@H](C[C@@H]5C)C)O)C[C@@H]4C)C)C)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 698.89 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
1: Lee W, Kang S, Jung B, Lee HS, Kang SH. Total synthesis of laidlomycin. Chem Commun (Camb). 2016 Feb 28;52(17):3536-9. doi: 10.1039/c5cc10673g. Epub 2016 Feb 4. PubMed PMID: 26842424. 2: Cernicchiaro N, Corbin M, Quinn M, Prouty F, Branine M, Renter DG. Meta-analysis of the effects of laidlomycin propionate, fed alone or in combination with chlortetracycline, compared with monensin sodium, fed alone or in combination with tylosin, on growth performance, health, and carcass outcomes in finishing steers in North America. J Anim Sci. 2016 Apr;94(4):1662-76. doi: 10.2527/jas.2015-0086. PubMed PMID: 27136025. 3: Fan YK, Croom J, Eisen EJ, Spires HR, Daniel LR. Ionophores have limited effects on jejunal glucose absorption and energy metabolism in mice. J Anim Sci. 2003 Aug;81(8):2072-9. PubMed PMID: 12926789. 4: Bauer ML, Herold DW, Britton RA, Stock RA, Klopfenstein TJ, Yates DA. Efficacy of laidlomycin propionate to reduce ruminal acidosis in cattle. J Anim Sci. 1995 Nov;73(11):3445-54. PubMed PMID: 8586605. 5: Domescik EJ, Martin SA. Effects of laidlomycin propionate and monensin on the in vitro mixed ruminal microorganism fermentation. J Anim Sci. 1999 Aug;77(8):2305-12. PubMed PMID: 10462011. 6: Spires HR, Olmsted A, Berger LL, Fontenot JP, Gill DR, Riley JG, Wray MI, Zinn RA. Efficacy of laidlomycin propionate for increasing rate and efficiency of gain by feedlot cattle. J Anim Sci. 1990 Oct;68(10):3382-91. PubMed PMID: 2254209. 7: Spires HR, Algeo JW. Laidlomycin butyrate--an ionophore with enhanced intraruminal activity. J Anim Sci. 1983 Dec;57(6):1553-60. PubMed PMID: 6674292. 8: Gräfe U, Stengel C. On the role of 26-deoxylaidlomycin in laidlomycin biosynthesis. J Basic Microbiol. 1991;31(4):313-6. PubMed PMID: 1744816. 9: Wampler JL, Martin SA, Hill GM. Effects of laidlomycin propionate and monensin on glucose utilization and nutrient transport by Streptococcus bovis and Selenomonas ruminantium. J Anim Sci. 1998 Oct;76(10):2730-6. PubMed PMID: 9814916. 10: Nakamura M, Kunimoto S, Kawashima H, Takeuchi T, Ohno T. Inhibitory effect of laidlomycin on human immunodeficiency virus replication. J Antibiot (Tokyo). 2000 Sep;53(9):975-8. PubMed PMID: 11099233. 11: Edrington TS, Callaway TR, Bischoff KM, Genovese KJ, Elder RO, Anderson RC, Nisbet DJ. Effect of feeding the ionophores monensin and laidlomycin propionate and the antimicrobial bambermycin to sheep experimentally infected with E. coli O157:H7 and Salmonella typhimurium. J Anim Sci. 2003 Feb;81(2):553-60. PubMed PMID: 12643501. 12: Edrington TS, Callaway TR, Varey PD, Jung YS, Bischoff KM, Elder RO, Anderson RC, Kutter E, Brabban AD, Nisbet DJ. Effects of the antibiotic ionophores monensin, lasalocid, laidlomycin propionate and bambermycin on Salmonella and E. coli O157:H7 in vitro. J Appl Microbiol. 2003;94(2):207-13. PubMed PMID: 12534812. 13: Galyean ML, Malcolm KJ, Duff GC. Performance of feedlot steers fed diets containing laidlomycin propionate or monensin plus tylosin, and effects of laidlomycin propionate concentration on intake patterns and ruminal fermentation in beef steers during adaptation to a high-concentrate diet. J Anim Sci. 1992 Oct;70(10):2950-8. PubMed PMID: 1429270. 14: Bohnert DW, Harmon DL, Dawson KA, Larson BT, Richards CJ, Streeter MN. Efficacy of laidlomycin propionate in low-protein diets fed to growing beef steers: effects on steer performance and ruminal nitrogen metabolism. J Anim Sci. 2000 Jan;78(1):173-80. PubMed PMID: 10682819. 15: Gräfe U, Reinhardt G, Miosga N. Monovalent cation specificity of passive transport mediated by laidlomycin and 26-deoxylaidlomycin. J Basic Microbiol. 1989;29(6):391-4. PubMed PMID: 2614677. 16: Thompson AJ, Smith ZK, Corbin MJ, Harper LB, Johnson BJ. Ionophore strategy affects growth performance and carcass characteristics in feedlot steers. J Anim Sci. 2016 Dec;94(12):5341-5349. doi: 10.2527/jas.2016-0841. PubMed PMID: 28046158. 17: Clark RD, Maddox ML, Spires HR, Long PL. Laidlomycin phenylcarbamate, a semisynthetic polyether antibiotic. J Antibiot (Tokyo). 1986 Dec;39(12):1765-8. PubMed PMID: 3818449. 18: Yoo JC, Kim JH, Ha JW, Park NS, Sohng JK, Lee JW, Park SC, Kim MS, Seong CN. Production and biological activity of laidlomycin, anti-MRSA/VRE antibiotic from Streptomyces sp. CS684. J Microbiol. 2007 Feb;45(1):6-10. PubMed PMID: 17342048. 19: Humphry JB, Coffey KP, Moyert JL, Brazle FK, Lomas LW. Intake, digestion, and digestive characteristics of Neotyphodium coenophialum-infected and uninfected fescue by heifers offered hay diets supplemented with Aspergillus oryzae fermentation extract or laidlomycin propionate. J Anim Sci. 2002 Jan;80(1):225-34. PubMed PMID: 11831521. 20: Zinn RA, Alvarez EG, Montaño MF, Ramirez JE. Interaction of protein nutrition and laidlomycin on feedlot growth performance and digestive function in Holstein steers. J Anim Sci. 2000 Jul;78(7):1768-78. PubMed PMID: 10907818.

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