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CAS No. : | 71989-14-5 | MDL No. : | MFCD00037131 |
Formula : | C23H25NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FODJWPHPWBKDON-IBGZPJMESA-N |
M.W : | 411.45 | Pubchem ID : | 2724635 |
Synonyms : |
4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate;Fmoc-L-Asp(OtBu)-OH
|
Num. heavy atoms : | 30 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.35 |
Num. rotatable bonds : | 10 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 110.53 |
TPSA : | 101.93 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.32 cm/s |
Log Po/w (iLOGP) : | 2.84 |
Log Po/w (XLOGP3) : | 3.5 |
Log Po/w (WLOGP) : | 3.71 |
Log Po/w (MLOGP) : | 2.56 |
Log Po/w (SILICOS-IT) : | 3.32 |
Consensus Log Po/w : | 3.19 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.23 |
Solubility : | 0.0241 mg/ml ; 0.0000586 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.32 |
Solubility : | 0.00195 mg/ml ; 0.00000475 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.74 |
Solubility : | 0.000749 mg/ml ; 0.00000182 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.07 |
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 |
---|---|---|
62% | With [2-(dicyclohexylphosphino)ethyl]trimethylammonium chloride; phenylsilane In tetrahydrofuran; water at 20℃; for 2 h; Inert atmosphere | General procedure: A suspension of PdEnCat 30 (Aldrich; 0.4 mmol/g loading, 0.05 equiv) inTHF–H2O (9:1, 5 mL) was bubbled with argon for 10 min.After this time, DCHT (0.15 equiv) and the correspondingallyl ester 1 (1.0 equiv, 70 mg) were added under positivepressure. Finally, PhSiH3 was injected (2.0 equiv), and themixture was allowed to react for 2 h at r.t. under an argonatmosphere. After this time, the reaction was filtered throughCelite and the filtrate was evaporated under reducedpressure. The remaining solid was dissolved with EtOAc (20mL) and washed with H2O (3 × 10 mL) and brine (3 × 10mL). The organic layer was dried (MgSO4) and evaporatedunder vacuum. Purification by solid-phase extraction (C18reverse-phase chromatography, H2O/MeOH) gave purecarboxylic acids 2 (yields shown in Table 1). Purity wasdetermined by HPLC, 1H NMR and 13C NMR analyses. Allthe carboxylic acids are commercially available. Therecorded 1H and 13C NMR spectra of the synthesizedcompounds were consistent with those registered forcommercial samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Fmoc strategy based solid phase peptide synthesis procedure was employed for preparing the non-targeting control SNEHPSDK-lipopeptide 2 as depicted schematically in Scheme 2. 500 mg of H-Eys(l3oc)-2-ClTrt resin-i (M-Soc-Eysine pre-loaded 2-chioro trityl resin, 0.77-0.79 mmol/g loading) was first swelled in 10 mE DMF for 3 hand then coupled with Fmoc-Asp(O-tert-butyl) (2 equiv) using HETU (2 equiv) and DIPEA (4 equiv) in 10 mE DMF at room temperature for 1 .5 h to afford intermediate 2 (Scheme 2). The resin was washed with 10 mE DMF and the Fmoc group was removed with a solution of piperidine:DMF (1:4, v/v, 10 mE, 5 mi 2x) at room temperature. Following the same Fmoc strategy, sequential couplings of Fmoc-Ser(Otert-butyl)-OH, Fmoc-Pro-OH, Fmoc-His(Trt)-OH, FmocEcu-OH, Fmoc-Asn(Trt)-OH and l3oc-Ser(O-tert-butyl)-OH (2 equiv each) using HETU (2 equiv) and DIPEA (4 equiv) in DMF at room temperature for 1 .5 h for each amino acid afforded the resin associated octapeptide intermediate 3 (Scheme 2). The resin-bound octapeptide intermediate 3 (Scheme 2) was taken out of the reaction vessel in 10 mE DCM, washed thoroughly with DCM (5x10 mE) and dried well. The resulting dried resin bound intermediate 3 (Scheme 2) was treated with TFA:DCM (5:95, v/v, 100 mE) for 2 hat 0° C. to obtain a protected octapeptide intermediate 4 (0.37 g, 75percent yield). N, N-di-n-octadecyl-N-2-aminoeth- ylamine (0.08 g, 0.15 mmol) was then dissolved in 3 mE dry DCM and the solution was added to an ice cold reaction mixture which has been under stirring for 30 mm containing EDCI (0.043 g, 0.23 mmol), HOST (0.034 g, 0.23 mmol), DIPEA (131 pL, 0.75 mmol) and the protected octapeptide intermediate 4 (0.33 g, 0.19 mmol) in dry DCM (5 mE). The resulting solution was lefi under stirring at room temperature for 12 h. The solvent was then evaporated in the rotary evaporator at 30° C. and the residue was dried completely under high vacuum. The dried intermediate was treated with TFA:DCM:TIS (90:5:5 v/v, 2 mE) for 3 h at 0° C. and washed with TFA:DCM (1:9, v/v, 10 mE). The acid washings were concentrated to about 1 mE and 14 mE acetone was added until a white precipitate separated. Same precipitation process was repeated five times with 14 mE acetone each time and the final precipitate was washed two times with 14 mE of dietheylether each time. The precipitate upon chloride ion exchange chromatography over 5 g Amberlyst IRA-400 resin followed by purification with reversed phase HPEC afforded the pure SNEHPSDK-lipopeptide 2 as a white, solid (188 mg, 47percent yield based on octapeptide intermediate 4 shown in Scheme 2). The purified SNEHPSDK-lipopeptide 2 was characterized by the molecular ion peak in ESIMS and purity was confirmed by reversed phase analytical HPEC using two different mobile phases. ESIMS: mlz=1444 [M+1]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.7 g | A solution of (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert- butoxy)-4-oxobutanoic acid (10 g, 24.30 mmol) and <strong>[7149-75-9]4-chloro-3-methylaniline</strong> (5.16 g, 36.5 mmol) in DCM (150 mL) at 0 °C was treated with DIEA (16.93 ml, 97 mmol) and cooled to °C. After 10 min, HATU (18.48 g, 48.6 mmol) was added portionwise. The reaction mixture was stirred at 0 °C for 1 h and the reaction mixture was partitioned between EA (50 mL) and an aqueous 1 M HCl solution (200 mL). The layers were separated and the organic layer was re-washed with an aqueous 1 M HCl solution (2 x 200 mL) and brine (200 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated to 18.7 g (101percent) of Intermediate 17A as a beige solid. LCMS [m/z] calculated for C30H31ClN2O5: 534.2; found 557.2 [M+Na]+, tR=3.01 min (Method 4).1H NMR (400 MHz, DMSO- d6) delta 10.17 (s, 1H), 7.98? 7.78 (m, 3H), 7.78? 7.57 (m, 3H), 7.57? 7.29 (m, 6H), 4.50 (td, J = 8.4, 5.9 Hz, 1H), 4.43? 4.15 (m, 3H), 2.71 (dd, J = 15.9, 5.9 Hz, 1H), 2.55 (dd, J = 16.0, 8.7 Hz, 1H), 2.29 (s, 3H), 1.37 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | (0234) To enable investigation of introducing non-proteinogenic amino acids (listed in Figure 1) on A20FMDV2 binding activity, biotinylated peptides 1-15 (see Table 1), except for peptide 6, were synthesised by standard Fmoc SPPS on the acid liable (0235) hydroxymethylphenoxypropionic acid linker (HMPP) which delivers a C- terminal carboxylic acid using to the conditions depicted in Scheme 1. The desired peptide sequences were assembled using 20percent (0236) piperidine/DMF to remove the Fmoc protecting group and 0- (0237) (benzotriazol-l-yl) -N, N, N ' , N '-tetramethyluronium hexafluorophosphate (HBTU) / DIPEA as coupling reagents. (0238) Since specific binding to the nubetabeta integrin was to be studied by flow cytometry, the native alanine at the second residue in A20FMDV2 (1) and all analogues thereof, were substituted with a biotinylated lysine residue. This substitution has previously been shown to be well tolerated [24,25] . We chose to install the D-biotin moiety by selective deprotection of a 1- ( 4 , 4-dimethyl-2 , 6-dioxocyclohex-l- ylidene ) ethyl (Dde) [19] group on the side chain group followed by condensation with D-biotin using HBTU/DIPEA. (0239) Trifluoroacetic acid (TFA) /H2O/3, 6-dioxa-l , 8-octanedithiol (0240) (DODT) /triisopropylsilane (TIPS) (94:2.5:2.5:1.0, v/v/v/v) effected cleavage of the synthesised peptides from the corresponding (0241) peptidyl-resins . Peptides 1-15 were obtained in good yields ranging from 2percent-50percent and purity exceeding 99percent (see peptide characterization data) . (0242) For the synthesis of peptide 6 containing an i\7-L-methyllysine modification we employed an on-resin i\7-methylation protocol [22] which furnished peptide 6 in good yield (30percent) following TFA-mediated peptide cleavage and RP-HPLC purification. (0243) The lead peptide, A20FMDV2, which contains all naturally-occurring amino acids would be susceptible to degradation by exopeptidases which act on the amino- and carboxy terminuses. To mitigate this, six N- and/or C-terminus-modified and biotinylated A20FDMV2 mimics were prepared wherein we systematically modified the amino and carboxy ends (peptides 16-18) and the N-terminal and C-terminal amino acids (Asnl and Thr20, respectively, peptides 19-21) . N- terminal/C-terminal modified peptides 16-18 were obtained by capping of the N-terminus with acetic anhydride (16) or by employing the Rink amide linker to afford the C-terminal carboxamide (17) or a combination of both (peptide 18) . (0244) Peptide 19, bearing the unnatural D-Asnl in place of the native Asnl at the N-terminus of biotinylated A20FMDV2 (1) was obtained using the synthetic route outlined in Scheme 1 except that the Fmoc-D- Asn(Trt)-OH building block was incorporated into the synthesis as the N-terminal residue. For the preparation of peptides 20 and 21, which contains the unnatural D-Thr at the C-terminus, HMP-anchored resin 27 (see Scheme 1, HMP = hydroxymethylphenoxyacetic acid) was first esterified with Fmoc-D-Thr (tBu) -OH using DIC/DMAP and the sequence then elongated by Fmoc SPPS . (0245) Table 1. List of prepared synthetic peptides [N-term] - XiK (Biotin) VPNLRGDLQVX2AQX3VARX4- [C-term] containing substitutions for the native Lysl6 (peptides 2-6) or Leul3 (peptides 7-15), C- terminal/N-terminal variants (peptides 16-21) and DTPA-modified peptides (22-26) . NB: nomenclature, particularly X position (0246) numbering used in this table is not the same as that used in the claims . (0247) Compound N- Xl X2 X3 X4 C- term. term. (0248) 1 NH2 Asn Leu Lys Thr C02H (0249) 2 NH2 Asn Leu D-Lys Thr C02H (0250) 3 NH2 Asn Leu L-Orn Thr C02H (0251) 1-2,4- (0252) 4 NH2 Asn Leu diaminobutyric Thr C02H acid (0253) 1-2,3- (0254) 5 NH2 Asn Leu diaminopropionic Thr C02H acid (0255) 6 NH2 Asn Leu ZV-L-meth llysine Thr C02H (0256) 7 NH2 Asn aminoisobutyric Lys Thr C02H acid (0257) 8 NH2 Asn L-norvaline Lys Thr C02H (0258) 9 NH2 Asn L-norleucine Lys Thr C02H (0259) 10 NH2 Asn L-allylglycine Lys Thr C02H (0260) L-tert- (0261) 11 NH2 Asn Lys Thr C02H butylalanine (0262) 12 NH2 Asn L-homoleucine Lys Thr C02H (0263) L-2-amino-3- (0264) 13 NH2 Asn ethylpentanoic Lys Thr C02H acid (0265) L- (0266) 14 NH2 Asn Lys Thr C02H cyclohexylalanine (0267) 15 L- (0268) NH2 Asn Lys Thr C02H adamantylglycine (0269) 16 Ac-NH Asn Leu Lys Thr C02H (0270) 17 NH2 Asn Leu Lys Thr CONH2 (0271) 18 Ac-NH Asn Leu Lys Thr CONH2 (0272) 19 D- (0273) NH2 Leu Lys Thr C02H (0274) Asn (0275) 20 D- (0276) NH2 Asn Leu Lys C02H (0277) Thr (0278) 21 D- D- (0279) NH2 Leu Lys C02H (0280) Asn Thr (0281) 22 DTPA- (0282) Asn Leu Lys Thr C02H NH (0283) 23 DTPA- (0284) Asn Leu Lys Thr C02H Gly-NH (0285) 24 DTPA- (0286) Asn Leu Lys Thr CONH2 NH (0287) 25 DTPA- D- (0288) Leu Lys Thr C02H NH Asn (0289) 26 DTPA- D- D- (0290) Leu Lys C02H NH Asn Thr (0291) 1 D -yrpercent \?Q ^ (0292) ? -^H Q ? (0293) (0294) Scheme 1. Synthetic protocol for the preparation of the biotinylated A20FMDV2 peptide variants. (0295) The results obtained from th... |
Tags: 71989-14-5 synthesis path| 71989-14-5 SDS| 71989-14-5 COA| 71989-14-5 purity| 71989-14-5 application| 71989-14-5 NMR| 71989-14-5 COA| 71989-14-5 structure
[ 180675-08-5 ]
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4-((3-methylpentan-3-yl)oxy)-4-oxobutanoic acid
Similarity: 0.96
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