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CAS No. : | 157355-81-2 | MDL No. : | MFCD00153365 |
Formula : | C19H19NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OYULCCKKLJPNPU-APPDUMDISA-N |
M.W : | 341.36 | Pubchem ID : | 6992532 |
Synonyms : |
(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-threonine
|
Num. heavy atoms : | 25 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.26 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 91.14 |
TPSA : | 95.86 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.65 cm/s |
Log Po/w (iLOGP) : | 2.04 |
Log Po/w (XLOGP3) : | 2.44 |
Log Po/w (WLOGP) : | 2.36 |
Log Po/w (MLOGP) : | 1.74 |
Log Po/w (SILICOS-IT) : | 2.15 |
Consensus Log Po/w : | 2.15 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -3.39 |
Solubility : | 0.14 mg/ml ; 0.00041 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.1 |
Solubility : | 0.0274 mg/ml ; 0.0000801 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.35 |
Solubility : | 0.0152 mg/ml ; 0.0000446 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.94 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
H-Ala-Trt(2-Cl)-resin (5 g, 3 mmol, pre-swelled in CH2C12) was treated with a solution of <strong>[157355-81-2]Fmoc-D-Thr-OH</strong> (2.05 g, 6 mmol), HBTU (2.28 g, 6 mmol), and NEt3 (1.6 mL, 12 mmol) in 1:1 DMF/CH2C12 (25 mL). After the resin suspension was mixed for 1 hour, the resin was filtered and washed with DMF. Complete conversion was confirmed by a negative Kaiser test. The resin was then treated with 20% piperidine in DMF (40 mL) for two 15-minute cycles, after which the resin was washed with DMF. Finally, the resin was treated with a solution ofAlloc-Osu (0.93 mL, 6 mmol) and NEt3 (1.21 mL, 9 mmol) in 1:1 DMF/CH2C12 (25 mL). After the resin suspension was mixed for 1.5 hours, the resin was filtered and washed with DMF. Complete conversion was confirmed by anegative Kaiser test. The resin was dried and used in portions for subsequent chemistry. The resin-bound peptide obtained above (1 mmol, pre-swelled in CH2C12) wastreated with a solution of Fmoc-Ile-OH (2.12 g, 6 mmol) and DMAP (73 mg, 0.6 mmol) in 4:1 CH2C12/NMP (10 mL). The reaction was then initiated by the addition of DIC (0.93 mL, 6 mmol). After the reaction was mixed for 3 hours, the resin was filtered andwashed with CH2C12. Complete conversion to the isoleucyl ester was confirmed by LCMS. Analytical HPLC indicated <5% Ile c carbon epimerization (Gradient: 30-100% B over 10 minutes at 2 mL/min). LCMS analysis - ESI mlz observed: 610.1; required for [C32H39N309 + H]: 610.3.The resin-bound peptide obtained above (1 mmol, pre-swelled in CH2C12) wastreated with 20% piperidine in DMF for two 15-minute cycles, after which the resin waswashed thoroughly with DMF. A solution of O-nitrobenzenesulfonyl chloride (663 mg, 3 mmol) and 2,4,6-collidine (1.19 mL, 9 mmol) in DMF (15 mL) was added to the resin and mixed for 2 hours. The resin was then filtered and washed with DMF and DCM. Complete conversion was confirmed by a negative Kaiser test.The resin-bound peptide obtained above (1 mmol) was pre-swelled in CH2C12 and the solid phase reaction vessel was drained by purging with argon for 5 minutes. The resin was then treated with a solution of Pd(PPh3)4 (231 mg, 0.2 mmol) in CH2C12 (15 mL) followed by phenylsilane (1.5 mL, 12 mmol). The reaction was mixed for 1 hour with occasional venting to relieve pressure buildup inside the reaction vessel. The resinwas filtered and washed with DCM, NMP, and DMF. Complete removal of the alloc protecting group was confirmed by LCMS. LCMS analysis - ESI mlz+ observed: 489.4; required for [C19H28N409S + H]:489.2.The resin-bound peptide obtained above was then treated with a solution of FmocSer(tBu)-OH (1.14 g, 3 mmol), HOBt hydrate (462 mg, 3 mmol), and DIC (464 tL, 3 mmol) in DMF (15 mL). After the reaction was mixed overnight, the resin was filtered and washed with DMF. Complete conversion was confirmed by a negative Kaiser test. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In many embodiments, Arg10-teixobactin and other homologues were synthesized by SPPS on 2-chlorotrityl chloride resin, followed by solution-phase macrolactamization to form the Arg10-Ile11 amide bond (FIG. 25). Fmoc protecting groups were used to construct all of the amide bonds and carried D-Thr8 through the entire synthesis without side chain protection. All homologues were prepared and studied as the trifluoroacetic acid (TFA) salts. The synthesis began by attaching Fmoc-Arg(Pbf)-OH to 2-chlorotrityl chloride resin. Residues 9 through 1 were then introduced by standard Fmoc-based SPPS using HCTU as the coupling reagent. D-Thr8 was introduced without a protecting group at the hydroxy position. No O-acylation of D-Thr8 was observed in the subsequent rounds of SPPS. D-Thr8 was then O-acylated with Fmoc-Ile-OH using DIC and DMAP. Fmoc-deprotection, followed by cleavage from the resin with 20% hexafluoroisopropanol (HFIP) in CH2Cl2 afforded the linear precursor. Macrolactamization with HBTU and HOBt, followed by global deprotection with trifluoroacetic acid (TFA) and RP-HPLC purification afforded Arg10-teixobactin. A series of homologues were also prepared using similar procedures. The details of the Arg10-teixobactin synthesis are described in the subsequent paragraphs. Resin Loading. 2-Chlorotrityl chloride resin (300 mg, 1.2 mmol/g) was added to a 10 mL Bio-Rad Poly-Prep chromatography column. The resin was suspended in dry CH2Cl2 (10 mL) and allowed to swell for 30 min. The resin was loaded with a solution of Fmoc-Arg(Pbf)-OH (117 mg, 0.18 mmol, 0.50 equiv) and 2,4,6-collidine (300 muL) in dry CH2Cl2 (5 mL). The suspension was agitated for 12 h. The solution was drained, and the resin was washed with dry CH2Cl2 (3×). A mixture of CH2Cl2/MeOH/DIPEA (17:2:1, 8 mL) was added to the resin and agitated for 1 h to cap any unreacted resin sites. The solution was drained, and the resin was washed with dry CH2Cl2 (3×). The resin loading was determined to be 0.09 mmol [0.29 mmol/g, 48% loading] through UV analysis of the Fmoc cleavage product. Peptide Coupling. The loaded resin was suspended in dry DMF and transferred to a solid-phase peptide synthesis reaction vessel for automated peptide coupling with Fmoc-protected amino acid building blocks. The linear peptide was synthesized through the following cycles: i. Fmoc deprotection with 20% (v/v) piperidine in dry DMF (3 mL) for 10 min, ii. resin washing with dry DMF (3×), iii. coupling of amino acid (0.36 mmol, 4 equiv) with HCTU (142 mg, 0.36 mmol, 4 equiv) in 20% (v/v) 2,4,6-collidine in dry DMF (3 mL) for 20 min, and iv. resin washing with dry DMF (6×). For D-to-L and L-to-D amino acid couplings, the reaction time in step iii was increased to 1 h. After completing the linear synthesis, the resin was transferred to a 10 mL Bio-Rad Poly-Prep chromatography column. The resin was then washed with dry DMF (3×) and dry CH2Cl2 (3×). Esterification. In a test tube, Fmoc-Ile-OH (303 mg, 0.90 mmol, 10 equiv) and diisopropylcarbodiimide (140 muL, 0.90 mmol, 10 equiv) were dissolved in dry CH2Cl2 (5 mL). The resulting solution was filtered through 0.20 mum nylon filter, and then 4-dimethylaminopyridine (11 mg, 0.09 mmol, 1 equiv) was added to the filtrate. The resulting solution was transferred to the resin and was gently agitated for 1 h. The solution was drained and the resin was washed with dry CH2Cl2 (3×) and DMF (3×). Fmoc Deprotection and Cleavage of the Linear from the Resin. The Fmoc protecting group on Ile11 was removed by adding 20% piperidine in dry DMF (5 mL) for 30 min. The solution was drained, and the resin was washed with dry DMF (3×) and then with dry CH2Cl2 (3×). To cleave the peptide, the resin was treated with 20% hexafluoroisopropanol in dry CH2Cl2 (6 mL) followed by gentle agitation for 1 h. The filtrate was collected in a round-bottomed flask. The resin was washed with a second aliquot of 20% hexafluoroisopropanol (6 mL) and then washed with dry CH2Cl2 (3×). The filtrates were combined and concentrated under reduced pressure to afford a clear oil. The oil was placed under vacuum (10 mTorr) to remove any residual solvents. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Fmoc-Ile-OH With 2,4,6-trimethyl-pyridine In dichloromethane Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: N-tert-butoxycarbonyl-N-methyl-D-phenylalanine; N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine; Fmoc-Ser(tBu)-OH; Fmoc-Ile-OH; (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid; (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine; trifluoroacetic acid; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; N-fluorenylmethoxycarbonyl-N’-trityl-D-glutamine Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine With 2,4,6-trimethyl-pyridine In dichloromethane Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; Stage #3: N-tert-butoxycarbonyl-N-methyl-D-phenylalanine; N-(9-Fluorenylmethoxycarbonyl)-D-alloisoleucine; Fmoc-Ser(tBu)-OH; Fmoc-Ile-OH; (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid; (((9H-fluoren-9-yl)methoxy)carbonyl)-D-threonine; N-fluorenylmethoxycarbonyl-N’-trityl-D-glutamine Further stages; |
[ 940301-35-9 ]
(2S,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-4-methylpentanoic acid
Similarity: 0.96
[ 1217603-41-2 ]
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-methylbutanoic acid
Similarity: 0.95
[ 884880-39-1 ]
(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-3-methylbutanoic acid
Similarity: 0.95
[ 158257-40-0 ]
(3S,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-6-methylheptanoic acid
Similarity: 0.94
[ 131545-63-6 ]
(2R,3S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(benzyloxy)butanoic acid
Similarity: 0.92
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P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
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H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
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H240 | Heating may cause an explosion |
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H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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Health hazards | |
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H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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