Bulgecin C | CAS#92953-56-5 | glycopeptide

MedKoo Cat#: 597876 | Name: Bulgecin C

Description:

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

Bulgecin C is an O-sulfonated glycopeptides that are able to enhance the antibacterial activity of beta-lactam antibiotics.

Chemical Structure

Bulgecin C

CAS#92953-56-5

Theoretical Analysis

MedKoo Cat#: 597876

Name: Bulgecin C

CAS#: 92953-56-5

Chemical Formula: C14H24N2O12S

Exact Mass: 444.1050

Molecular Weight: 444.40

Elemental Analysis: C, 37.84; H, 5.44; N, 6.30; O, 43.20; S, 7.21

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 #

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Synonym

Bulgecin C;

IUPAC/Chemical Name

(2S,4S,5R)-4-(((2R,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-(sulfooxy)tetrahydro-2H-pyran-2-yl)oxy)-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

InChi Key

FKTBPFXEHOYGEZ-IZHHZIKYSA-N

InChi Code

InChI=1S/C14H24N2O12S/c1-5(19)15-10-11(20)12(28-29(23,24)25)9(4-18)27-14(10)26-8-2-6(13(21)22)16-7(8)3-17/h6-12,14,16-18,20H,2-4H2,1H3,(H,15,19)(H,21,22)(H,23,24,25)/t6-,7+,8-,9+,10+,11+,12+,14+/m0/s1

SMILES Code

O=C(O)[C@H]1N[C@H](CO)[C@@H](O[C@H]2[C@H](NC(C)=O)[C@H]([C@@H]([C@@H](CO)O2)OS(=O)(O)=O)O)C1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 444.40 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.

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: Thunnissen AM, Rozeboom HJ, Kalk KH, Dijkstra BW. Structure of the 70-kDa soluble lytic transglycosylase complexed with bulgecin A. Implications for the enzymatic mechanism. Biochemistry. 1995 Oct 3;34(39):12729-37. PubMed PMID: 7548026. 2: Karlsen S, Hough E. Structure of a complex between bulgecin, a bacterial metabolite, and lysozyme from the rainbow trout. Acta Crystallogr D Biol Crystallogr. 1996 Jan 1;52(Pt 1):115-23. PubMed PMID: 15299732. 3: Karlsen S, Hough E, Rao ZH, Isaacs NW. Structure of a bulgecin-inhibited g-type lysozyme from the egg white of the Australian black swan. A comparison of the binding of bulgecin to three muramidases. Acta Crystallogr D Biol Crystallogr. 1996 Jan 1;52(Pt 1):105-14. PubMed PMID: 15299731. 4: Fibriansah G, Gliubich FI, Thunnissen AM. On the mechanism of peptidoglycan binding and cleavage by the endo-specific lytic transglycosylase MltE from Escherichia coli. Biochemistry. 2012 Nov 13;51(45):9164-77. doi: 10.1021/bi300900t. Epub 2012 Oct 30. PubMed PMID: 23075328. 5: Tomoshige S, Dik DA, Akabane-Nakata M, Madukoma CS, Fisher JF, Shrout JD, Mobashery S. Total Syntheses of Bulgecins A, B, and C and Their Bactericidal Potentiation of the β-Lactam Antibiotics. ACS Infect Dis. 2018 Jun 8;4(6):860-867. doi: 10.1021/acsinfecdis.8b00105. Epub 2018 May 7. PubMed PMID: 29716193; PubMed Central PMCID: PMC5996343. 6: Heidrich C, Templin MF, Ursinus A, Merdanovic M, Berger J, Schwarz H, de Pedro MA, Höltje JV. Involvement of N-acetylmuramyl-L-alanine amidases in cell separation and antibiotic-induced autolysis of Escherichia coli. Mol Microbiol. 2001 Jul;41(1):167-78. PubMed PMID: 11454209. 7: Khalaf JK, Datta A. An efficient and highly stereocontrolled route to bulgecinine hydrochloride. J Org Chem. 2004 Jan 23;69(2):387-90. PubMed PMID: 14725451. 8: Shinagawa S, Maki M, Kintaka K, Imada A, Asai M. Isolation and characterization of bulgecins, new bacterial metabolites with bulge-inducing activity. J Antibiot (Tokyo). 1985 Jan;38(1):17-23. PubMed PMID: 3918981. 9: Arends K, Celik EK, Probst I, Goessweiner-Mohr N, Fercher C, Grumet L, Soellue C, Abajy MY, Sakinc T, Broszat M, Schiwon K, Koraimann G, Keller W, Grohmann E. TraG encoded by the pIP501 type IV secretion system is a two-domain peptidoglycan-degrading enzyme essential for conjugative transfer. J Bacteriol. 2013 Oct;195(19):4436-44. doi: 10.1128/JB.02263-12. Epub 2013 Aug 2. PubMed PMID: 23913323; PubMed Central PMCID: PMC3807477. 10: Vijayaraghavan J, Kumar V, Krishnan NP, Kaufhold RT, Zeng X, Lin J, van den Akker F. Structural studies and molecular dynamics simulations suggest a processive mechanism of exolytic lytic transglycosylase from Campylobacter jejuni. PLoS One. 2018 May 14;13(5):e0197136. doi: 10.1371/journal.pone.0197136. eCollection 2018. PubMed PMID: 29758058; PubMed Central PMCID: PMC5951611.