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MedKoo Cat#: 574143 | Name: Feglymycin
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Description:

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

Feglymycin is a 13-amino acid peptide that has antibacterial and antiviral activities. It is active against Gram-positive bacteria and inhibits HIV viral replication.

Chemical Structure

Feglymycin
Feglymycin
CAS#209335-49-9

Theoretical Analysis

MedKoo Cat#: 574143

Name: Feglymycin

CAS#: 209335-49-9

Chemical Formula: C95H97N13O30

Exact Mass: 1899.6464

Molecular Weight: 1900.88

Elemental Analysis: C, 60.03; H, 5.14; N, 9.58; O, 25.25

Price and Availability

Size Price Availability Quantity
1mg USD 700.00 2 Weeks
5mg USD 2,000.00 2 Weeks
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Related CAS #
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Synonym
Feglymycin
IUPAC/Chemical Name
(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-2-(3,5-dihydroxyphenyl)acetyl]amino]-3-methylbutanoyl]amino]-2-(3,5-dihydroxyphenyl)acetyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-2-(3,5-dihydroxyphenyl)acetyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-2-(3,5-dihydroxyphenyl)acetyl]amino]-3-methylbutanoyl]amino]-2-(3,5-dihydroxyphenyl)acetyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-phenylpropanoyl]amino]butanedioic acid
InChi Key
QJQKBRUTBCTBKE-OVYRLPCXSA-N
InChi Code
InChI=1S/C95H97N13O30/c1-43(2)73(99-90(132)78(50-27-59(113)37-60(114)28-50)101-84(126)72(96)46-10-18-55(109)19-11-46)85(127)106-81(53-33-65(119)40-66(120)34-53)93(135)103-77(49-16-24-58(112)25-17-49)89(131)108-82(54-35-67(121)41-68(122)36-54)94(136)104-76(48-14-22-57(111)23-15-48)88(130)107-79(51-29-61(115)38-62(116)30-51)91(133)100-74(44(3)4)86(128)105-80(52-31-63(117)39-64(118)32-52)92(134)102-75(47-12-20-56(110)21-13-47)87(129)97-69(26-45-8-6-5-7-9-45)83(125)98-70(95(137)138)42-71(123)124/h5-25,27-41,43-44,69-70,72-82,109-122H,26,42,96H2,1-4H3,(H,97,129)(H,98,125)(H,99,132)(H,100,133)(H,101,126)(H,102,134)(H,103,135)(H,104,136)(H,105,128)(H,106,127)(H,107,130)(H,108,131)(H,123,124)(H,137,138)/t69-,70-,72+,73-,74-,75-,76-,77-,78+,79+,80+,81+,82+/m0/s1
SMILES Code
OC1=CC=C([C@@H](N)C(N[C@H](C2=CC(O)=CC(O)=C2)C(N[C@@H](C(C)C)C(N[C@H](C3=CC(O)=CC(O)=C3)C(N[C@@H](C4=CC=C(O)C=C4)C(N[C@H](C5=CC(O)=CC(O)=C5)C(N[C@@H](C6=CC=C(O)C=C6)C(N[C@@H](C(N[C@@H](C(C)C)C(N[C@H](C7=CC(O)=CC(O)=C7)C(N[C@@H](C8=CC=C(O)C=C8)C(N[C@H](C(N[C@H](C(O)=O)CC(O)=O)=O)CC9=CC=CC=C9)=O)=O)=O)=O)C%10=CC(O)=CC(O)=C%10)=O)=O)=O)=O)=O)=O)=O)C=C1
Appearance
Solid powder
Purity
>95% (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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,900.88 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: Rausch S, Hänchen A, Denisiuk A, Löhken M, Schneider T, Süssmuth RD. Feglymycin is an inhibitor of the enzymes MurA and MurC of the peptidoglycan biosynthesis pathway. Chembiochem. 2011 May 16;12(8):1171-3. doi: 10.1002/cbic.201100120. Epub 2011 Apr 28. PMID: 21538763. 2: Férir G, Hänchen A, François KO, Hoorelbeke B, Huskens D, Dettner F, Süssmuth RD, Schols D. Feglymycin, a unique natural bacterial antibiotic peptide, inhibits HIV entry by targeting the viral envelope protein gp120. Virology. 2012 Nov 25;433(2):308-19. doi: 10.1016/j.virol.2012.08.007. Epub 2012 Sep 7. PMID: 22959895. 3: Vértesy L, Aretz W, Knauf M, Markus A, Vogel M, Wink J. Feglymycin, a novel inhibitor of the replication of the human immunodeficiency virus. Fermentation, isolation and structure elucidation. J Antibiot (Tokyo). 1999 Apr;52(4):374-82. doi: 10.7164/antibiotics.52.374. PMID: 10395273. 4: Fuse S, Mifune Y, Nakamura H, Tanaka H. Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation. Nat Commun. 2016 Nov 28;7:13491. doi: 10.1038/ncomms13491. PMID: 27892469; PMCID: PMC5133696. 5: Gonsior M, Mühlenweg A, Tietzmann M, Rausch S, Poch A, Süssmuth RD. Biosynthesis of the Peptide Antibiotic Feglymycin by a Linear Nonribosomal Peptide Synthetase Mechanism. Chembiochem. 2015 Dec;16(18):2610-4. doi: 10.1002/cbic.201500432. Epub 2015 Oct 30. PMID: 26515424. 6: Dettner F, Hänchen A, Schols D, Toti L, Nusser A, Süssmuth RD. Total synthesis of the antiviral peptide antibiotic feglymycin. Angew Chem Int Ed Engl. 2009;48(10):1856-61. doi: 10.1002/anie.200804130. PMID: 19180618. 7: Hänchen A, Rausch S, Landmann B, Toti L, Nusser A, Süssmuth RD. Alanine scan of the peptide antibiotic feglymycin: assessment of amino acid side chains contributing to antimicrobial activity. Chembiochem. 2013 Mar 18;14(5):625-32. doi: 10.1002/cbic.201300032. Epub 2013 Feb 27. PMID: 23447362. 8: Bunkóczi G, Vértesy L, Sheldrick GM. The antiviral antibiotic feglymycin: first direct-methods solution of a 1000+ equal-atom structure. Angew Chem Int Ed Engl. 2005 Feb 18;44(9):1340-2. doi: 10.1002/anie.200461933. PMID: 15674989. 9: Yushchuk O, Binda E, Marinelli F. Glycopeptide Antibiotic Resistance Genes: Distribution and Function in the Producer Actinomycetes. Front Microbiol. 2020 Jun 17;11:1173. doi: 10.3389/fmicb.2020.01173. PMID: 32655512; PMCID: PMC7325946. 10: Gordts SC, Férir G, D'huys T, Petrova MI, Lebeer S, Snoeck R, Andrei G, Schols D. The Low-Cost Compound Lignosulfonic Acid (LA) Exhibits Broad-Spectrum Anti-HIV and Anti-HSV Activity and Has Potential for Microbicidal Applications. PLoS One. 2015 Jul 1;10(7):e0131219. doi: 10.1371/journal.pone.0131219. PMID: 26132818; PMCID: PMC4488490. 11: Henrich E, Ma Y, Engels I, Münch D, Otten C, Schneider T, Henrichfreise B, Sahl HG, Dötsch V, Bernhard F. Lipid Requirements for the Enzymatic Activity of MraY Translocases and in Vitro Reconstitution of the Lipid II Synthesis Pathway. J Biol Chem. 2016 Jan 29;291(5):2535-46. doi: 10.1074/jbc.M115.664292. Epub 2015 Nov 30. PMID: 26620564; PMCID: PMC4732233. 12: Newton PO, Ohashi M, Bastrom TP, Bartley CE, Yaszay B, Marks MC, Betz R, Lenke LG, Clements D. Prospective 10-year follow-up assessment of spinal fusions for thoracic AIS: radiographic and clinical outcomes. Spine Deform. 2020 Feb;8(1):57-66. doi: 10.1007/s43390-019-00015-1. Epub 2020 Jan 8. PMID: 31925756.

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