| Size | Price | |
|---|---|---|
| 1mg | ||
| Other Sizes |
| 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]
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| References | |
| 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] |
| 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
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| CAS # |
209335-49-9
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| PubChem CID |
25256761
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| 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
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| Appearance |
Typically exists as solid at room temperature
|
| LogP |
8.869
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| 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
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| 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
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| 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
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| 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;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| 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
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (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 |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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