Physicochemical Properties
| Molecular Formula | C95H97N13O30 |
| Molecular Weight | 1900.86 |
| Exact Mass | 1899.65 |
| Elemental Analysis | C, 60.03; H, 5.14; N, 9.58; O, 25.25 |
| CAS # | 209335-49-9 |
| PubChem CID | 25256761 |
| Sequence |
{d-nTyr}-{d-Phg(3,5-OH)}-Val-{d-Phg(3,5-OH)}-{nTyr}-{d-Phg(3,5-OH)}-{nTyr}-{d-Phg(3,5-OH)}-Val-{d-Phg(3,5-OH)}-{nTyr}-Phe-Asp H-D-nTyr-D-Phg(3,5-diOH)-Val-D-Phg(3,5-diOH)-nTyr-D-Phg(3,5-diOH)-nTyr-D-Phg(3,5-diOH)-Val-D-Phg(3,5-diOH)-nTyr-Phe-Asp-OH D-nortyrosyl-2-(3,5-dihydroxyphenyl)-D-glycyl-L-valyl-2-(3,5-dihydroxyphenyl)-D-glycyl-L-nortyrosyl-2-(3,5-dihydroxyphenyl)-D-glycyl-L-nortyrosyl-2-(3,5-dihydroxyphenyl)-D-glycyl-L-valyl-2-(3,5-dihydroxyphenyl)-D-glycyl-L-nortyrosyl-L-phenylalanyl-L-aspartic acid |
| SequenceShortening | {d-nTyr}-{d-Phg(3,5-OH)}-V-{d-Phg(3,5-OH)}-{nTyr}-{d-Phg(3,5-OH)}-{nTyr}-{d-Phg(3,5-OH)}-V-{d-Phg(3,5-OH)}-{nTyr}-FD; XXVXXXXXVXXFD |
| Appearance | Typically exists as solid at room temperature |
| LogP | 8.869 |
| Hydrogen Bond Donor Count | 29 |
| Hydrogen Bond Acceptor Count | 31 |
| Rotatable Bond Count | 40 |
| Heavy Atom Count | 138 |
| Complexity | 4020 |
| Defined Atom Stereocenter Count | 13 |
| SMILES | C(O)(=O)[C@H](CC(O)=O)NC(=O)[C@@H](C1=CC(O)=CC(O)=C1)NC(=O)[C@H](C(C)C)NC(=O)C(C1=CC(O)=CC(O)=C1)NC(=O)C(C1=CC=C(O)C=C1)NC(=O)C(C1=CC(O)=CC(O)=C1)NC(=O)C(C1=CC=C(O)C=C1)NC(=O)C(C1=CC(O)=CC(O)=C1)NC(=O)[C@H](C(C)C)NC(=O)C(C1=CC(O)=CC(O)=C1)NC(=O)C(C1=CC=C(O)C=C1)N |
| 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 |
| 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 |
| Synonyms | Feglymycin; 209335-49-9; (2R)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-L-valyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-(2S)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-(2S)-2-(4-hydroxyphenyl)glycyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-L-valyl-(2R)-2-(3,5-dihydroxyphenyl)glycyl-(2S)-2-(4-hydroxyphenyl)glycyl-L-phenylalanyl-L-aspartic acid; Feglymicin (compound 30); BDBM119091; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | HIV replication; HIV |
| ln Vitro | The novel peptide feglymycin has been isolated from cultures of Streptomyces sp. DSM 11171 by solid phase extraction, size exclusion chromatography and repeated reversed-phase chromatography. The molecular weight was found to be 1900.90 g/mol and the molecular formula is C95H97Nl3O30. Feglymycin contains 13 amino acids of which four are 3-hydroxyphenylglycine and five are 3,5-dihydroxyphenylglycine residues. The structure of the linear peptide has been determined by 1H and 13C NMR spectroscopy. The sequence was confirmed by the observed mass spectroscopic fragmentation pattern. As well as having weak antibacterial activity, feglymycin inhibits the replication of the human immunodeficiency virus (HIV) in vitro. [1] |
| References |
[1]. 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. [2]. Total synthesis of the antiviral peptide antibiotic feglymycin. Angew Chem Int Ed Engl. 2009;48(10):1856-61. |
| Additional Infomation |
H-D-nTyr-D-Phg(3,5-diOH)-Val-D-Phg(3,5-diOH)-nTyr-D-Phg(3,5-diOH)-nTyr-D-Phg(3,5-diOH)-Val-D-Phg(3,5-diOH)-nTyr-Phe-Asp-OH has been reported in Streptomyces with data available. An adaptable approach: The first highly convergent stereoselective synthesis of feglymycin (see structure) and its enantiomer is based on the coupling of repeating peptide fragments. The use of weakly basic conditions throughout the synthesis suppressed the epimerization of sensitive aryl glycine units. Feglymycin has strong anti-HIV activity as well as potent (previously identified as weak) antibacterial activity against Staphylococcus aureus. [2] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.5261 mL | 2.6304 mL | 5.2608 mL | |
| 5 mM | 0.1052 mL | 0.5261 mL | 1.0522 mL | |
| 10 mM | 0.0526 mL | 0.2630 mL | 0.5261 mL |