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[ CAS No. 166108-71-0 ] {[proInfo.proName]}

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Chemical Structure| 166108-71-0
Chemical Structure| 166108-71-0
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Product Citations

Product Citations      Expand+

Abeywardana, Maheeshi Yapa ; Whedon, Samuel D ; Lee, Kwangwoon , et al. DOI: PubMed ID:

Abstract: Sirtuin 2 (Sirt2) is a member of the family of NAD-dependent lysine deacylases and plays important roles in regulation of the and gene expression. As a nucleocytoplasmic deacetylase, Sirt2 has been shown to target both histone and non-histone acetylated protein substrates. The central catalytic domain of Sirt2 is flanked by flexible N- and C-termini, which vary in length and composition with alternative splicing. These termini are further subject to posttranslational modifications (PTMs) including phosphorylation. Here we investigate the function of the N- and C-termini on deacetylation of nuclear substrates by Sirt2. Remarkably, we find that the C-terminus autoinhibits deacetylation, while the N-terminus enhances deacetylation of proteins and , but not nucleosomes—a chromatin model substrate. Using protein semisynthesis we characterize the effect of cell cycle-linked N-terminal phosphorylation at two major phosphorylation sites (Ser23/Ser25) and find that these further enhance protein/peptide deacetylation, with no effect on nucleosome deacetylation. Additionally, we find that VRK1, an established binding partner of both Sirt2 and nucleosomes, can stimulate deacetylation of nucleosomes by Sirt2, likely through an electrostatic mechanism. Taken together, these findings reveal multiple mechanisms regulating the activity of Sirt2, which allow for a broad range of activities across its multiple biological roles.

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Erin M. Euliano ; Brett H. Pogostin ; Anushka Agrawal , et al. DOI:

Abstract: Toll-like receptors (TLRs) recognize pathogen- and damage-associated molecular patterns and, in turn, trigger the release of cytokines and other immunostimulatory molecules. As a result, TLR agonists are increasingly being investigated as vaccine adjuvants, though many of these agonists are small molecules that quickly diffuse away from the vaccination site, limiting their co-localization with antigens and, thus, their effect. Here, the small-molecule TLR7 agonist 1V209 is conjugated to a positively-charged multidomain peptide (MDP) hydrogel, K2, which was previously shown to act as an adjuvant promoting humoral immunity. Mixing the 1V209-conjugated K2 50:50 with the unfunctionalized K2 produces hydrogels that retain the shear-thinning and self-healing physical properties of the original MDP, while improving the solubility of 1V209 more than 200-fold compared to the unconjugated molecule. When co-delivered with ovalbumin as a model antigen, 1V209-functionalized K2 produces antigen-specific IgG titers that were statistically similar to alum, the gold standard adjuvant, and a significantly lower ratio of Th2-associated IgG1 to Th1-associated IgG2a than alum, suggesting a more balanced Th1 and Th2 response. Together, these results suggest that K2 MDP hydrogels functionalized with 1V209 are a promising adjuvant for vaccines against infectious diseases, especially those benefiting from a combined Th1 and Th2 immune response.

Keywords: vaccine adjuvant ; 1V209 ; TLR7 ; peptide hydrogel ; supramolecular

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Product Details of [ 166108-71-0 ]

CAS No. :166108-71-0 MDL No. :MFCD01321015
Formula : C21H23NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :XQPYRJIMPDBGRW-UHFFFAOYSA-N
M.W : 385.41 Pubchem ID :2756092
Synonyms :
Fmoc-NH-PEG2-CH2COOH
Chemical Name :1-(9H-Fluoren-9-yl)-3-oxo-2,7,10-trioxa-4-azadodecan-12-oic acid

Calculated chemistry of [ 166108-71-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 28
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.33
Num. rotatable bonds : 12
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 101.76
TPSA : 94.09 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.04
Log Po/w (XLOGP3) : 2.36
Log Po/w (WLOGP) : 2.64
Log Po/w (MLOGP) : 1.39
Log Po/w (SILICOS-IT) : 3.0
Consensus Log Po/w : 2.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.221 mg/ml ; 0.000573 mol/l
Class : Soluble
Log S (Ali) : -3.98
Solubility : 0.0407 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.91
Solubility : 0.00047 mg/ml ; 0.00000122 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.93

Safety of [ 166108-71-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 166108-71-0 ]

* 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.

  • Downstream synthetic route of [ 166108-71-0 ]

[ 166108-71-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • C41H39N2O3Pol [ No CAS ]
  • 3-(9-carboxy-nonyloxy)benzoic acid tert-butyl ester [ No CAS ]
  • [ 84793-07-7 ]
  • [ 35661-40-6 ]
  • [ 71989-23-6 ]
  • [ 62-57-7 ]
  • [ 32926-43-5 ]
  • [ 166108-71-0 ]
  • Fmoc-Arg(pg)-OH [ No CAS ]
  • Fmoc-Trp(pg)-OH [ No CAS ]
  • Fmoc-Gln(pg)-OH [ No CAS ]
  • Fmoc-Tyr(pg)-OH [ No CAS ]
  • Fmoc-Ser(pg)-OH [ No CAS ]
  • Fmoc-Asp(pg)-OH [ No CAS ]
  • Fmoc-Thr(pg)-OH [ No CAS ]
  • H-Aib-EGTFTSDVSSYLEGQAAK(Nε-{2-[2-(2-{2-[2-(2-{4-carboxy-4-[10-(3-carboxyphenoxy)decanoylamino]butyrylamino}ethoxy)ethoxy]acetylamino}ethoxy)ethoxy]acetyl})-EFIAWLVRGRK(Nε-{2-[2-(2-{2-[2-(2-{4-carboxy-4-[10-(3-carboxyphenoxy)decanoylamino]butyrylamino}ethoxy)ethoxy]acetylamino}ethoxy)ethoxy]acetyl})-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
SPPS method B refers to the synthesis of a protected peptidyl resin using Fmoc chemistry on a microwave based Liberty peptide synthesiser (CEM Corp., North Carolina). A suitable resin is a pre-loaded, low-load Wang resinavailable from Novabiochem (e.g. low load Fmoc-Lys(Mtt)-Wang resin, 0.35 mmol/g). Fmoc-deprotection was with 5percentpiperidine in NMP at up to 70 or 75°C. The coupling chemistry was DIC/HOAt in NMP. Amino acid/HOAt solutions (0.3M in NMP at a molar excess of 3-10 fold) were added to the resin followed by the same molar equivalent of DIC (0.75Min NMP). For example, the following amounts of 0.3M amino acid/HOAt solution were used per coupling for the followingscale reactions: Scale/ml, 0.10 mmol/2.5 ml, 0.25 mmol/5 ml, 1 mmol/15 ml. Coupling times and temperatures weregenerally 5 minutes at up to 70 or 75°C. Longer coupling times were used for larger scale reactions, for example 10min. Histidine amino acids were double coupled at 50°C, or quadruple coupled if the previous amino acid was stericallyhindered (e.g. Aib). Arginine amino acids were coupled at RT for 25 min then heated to 70 or 75°C for 5 min. Someamino acids such as but not limited to Aib, were "double coupled", meaning that after the first coupling (e.g. 5 min at75°C), the resin is drained and more reagents are added (amino acid, HOAt and DIC), and the mixture in heated again(e.g. 5 min at 75°C). When a chemical modification of a lysine side chain was desired, the lysine was incorporated asLys(Mtt). The Mtt group was removed by washing the resin with DCM and suspending the resin in neat (undiluted)hexafluoroisopropanol for 20 minutes followed by washing with DCM and NMP. The chemical modification of the lysinewas performed either by manual synthesis (see SPPS method D) or by one or more automated steps on the Libertypeptide synthesiser as described above, using suitably protected building blocks (see General methods), optionallyincluding a manual coupling. Preparation method: SPPS Method B, starting with low-load Fmoc-Lys(Mtt)-Wang resin. Fmoc-Lys(Mtt)-OH was used in position 26, and Boc-His(trt)-OH was used in position 7. The Mtt was removedwith HFIP, and 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid (commercially available from Iris Biotech),Fmoc-Glu-OtBu, and 3-(9-carboxy-nonyloxy)-benzoic acid tert-butyl ester were coupled using a double couplingmethod on the Liberty Peptide synthesiser.UPLC (method 04_A4_1): 10.01 minUPLC (method 08_B4_1): 8.81 minLCMS4: m/z = 978.5 (M+5H)5+, 1222.8 (M+4H)4+, 1630.1 (M+3H)3+
  • 2
  • [ 905303-12-0 ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • C41H39N2O3Pol [ No CAS ]
  • [ 84793-07-7 ]
  • [ 35661-40-6 ]
  • [ 71989-23-6 ]
  • [ 62-57-7 ]
  • [ 32926-43-5 ]
  • [ 166108-71-0 ]
  • Fmoc-Arg(pg)-OH [ No CAS ]
  • Fmoc-Trp(pg)-OH [ No CAS ]
  • Fmoc-Gln(pg)-OH [ No CAS ]
  • Fmoc-Tyr(pg)-OH [ No CAS ]
  • Fmoc-Ser(pg)-OH [ No CAS ]
  • Fmoc-Asp(pg)-OH [ No CAS ]
  • Fmoc-Thr(pg)-OH [ No CAS ]
  • H-Aib-EGTFTSDVSSYLEGQAAK(Nε-[2-(2-{2-[10-(4-carboxyphenoxy)decanoylamino]ethoxy}ethoxy)acetyl])-EFIAWLVRGRK(Nε-[2-(2-{2-[10-(4-carboxyphenoxy)decanoylamino]ethoxy}ethoxy)acetyl])-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
SPPS method B refers to the synthesis of a protected peptidyl resin using Fmoc chemistry on a microwave based Liberty peptide synthesiser (CEM Corp., North Carolina). A suitable resin is a pre-loaded, low-load Wang resinavailable from Novabiochem (e.g. low load Fmoc-Lys(Mtt)-Wang resin, 0.35 mmol/g). Fmoc-deprotection was with 5percentpiperidine in NMP at up to 70 or 75°C. The coupling chemistry was DIC/HOAt in NMP. Amino acid/HOAt solutions (0.3M in NMP at a molar excess of 3-10 fold) were added to the resin followed by the same molar equivalent of DIC (0.75Min NMP). For example, the following amounts of 0.3M amino acid/HOAt solution were used per coupling for the followingscale reactions: Scale/ml, 0.10 mmol/2.5 ml, 0.25 mmol/5 ml, 1 mmol/15 ml. Coupling times and temperatures weregenerally 5 minutes at up to 70 or 75°C. Longer coupling times were used for larger scale reactions, for example 10min. Histidine amino acids were double coupled at 50°C, or quadruple coupled if the previous amino acid was stericallyhindered (e.g. Aib). Arginine amino acids were coupled at RT for 25 min then heated to 70 or 75°C for 5 min. Someamino acids such as but not limited to Aib, were "double coupled", meaning that after the first coupling (e.g. 5 min at75°C), the resin is drained and more reagents are added (amino acid, HOAt and DIC), and the mixture in heated again(e.g. 5 min at 75°C). When a chemical modification of a lysine side chain was desired, the lysine was incorporated asLys(Mtt). The Mtt group was removed by washing the resin with DCM and suspending the resin in neat (undiluted)hexafluoroisopropanol for 20 minutes followed by washing with DCM and NMP. The chemical modification of the lysinewas performed either by manual synthesis (see SPPS method D) or by one or more automated steps on the Libertypeptide synthesiser as described above, using suitably protected building blocks (see General methods), optionallyincluding a manual coupling.Preparation method: SPPS method B, starting with low-load Fmoc-Lys(Mtt)-Wang resin.Fmoc-Lys(Mtt)-OH was used in position 26, and Boc-His(trt)-OH was used in position 7. The Mtt was removed withHFIP, and 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid (commercially available from Iris Biotech)and 4-(9-carboxy-nonyloxy)-benzoic acid tert-butyl ester (prepared as described in Example 25, step 2 of WO2006/082204) were coupled using a double coupling method on the Liberty Peptide synthesiserUPLC (method 04_A3_1): 10.51 minLCMS4: m/z = 1085.2 (M+4H)4+, 1447.3 (M+3H)3+
  • 3
  • [ 905303-12-0 ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • C41H39N2O3Pol [ No CAS ]
  • [ 84793-07-7 ]
  • [ 35661-40-6 ]
  • [ 71989-23-6 ]
  • [ 62-57-7 ]
  • [ 32926-43-5 ]
  • [ 166108-71-0 ]
  • Fmoc-Arg(pg)-OH [ No CAS ]
  • Fmoc-Trp(pg)-OH [ No CAS ]
  • Fmoc-Gln(pg)-OH [ No CAS ]
  • Fmoc-Tyr(pg)-OH [ No CAS ]
  • Fmoc-Ser(pg)-OH [ No CAS ]
  • Fmoc-Asp(pg)-OH [ No CAS ]
  • Fmoc-Thr(pg)-OH [ No CAS ]
  • H-Aib-EGTFTSDVSSYLEGQAAK(Nε{2-[2-(2-{2-[2-(2-{(S)-4-Carboxy-4-[10-(4-carboxyphenoxy)decanoylamino]butyrylamino}ethoxy)ethoxy]acetylamino}ethoxy)ethoxy]acet yl})-EFIAWLVRGRK(Nε-{2-[2-(2-{2-[2-(2-{(S)-4-carboxy-4-[10-(4-carboxyphenoxy)decanoylamino]butyrylamino}ethoxy)ethoxy]acetylamino}ethoxy)ethoxy]acetyl})-OH [ No CAS ]
YieldReaction ConditionsOperation in experiment
SPPS method B refers to the synthesis of a protected peptidyl resin using Fmoc chemistry on a microwave based Liberty peptide synthesiser (CEM Corp., North Carolina). A suitable resin is a pre-loaded, low-load Wang resinavailable from Novabiochem (e.g. low load Fmoc-Lys(Mtt)-Wang resin, 0.35 mmol/g). Fmoc-deprotection was with 5percentpiperidine in NMP at up to 70 or 75°C. The coupling chemistry was DIC/HOAt in NMP. Amino acid/HOAt solutions (0.3M in NMP at a molar excess of 3-10 fold) were added to the resin followed by the same molar equivalent of DIC (0.75Min NMP). For example, the following amounts of 0.3M amino acid/HOAt solution were used per coupling for the followingscale reactions: Scale/ml, 0.10 mmol/2.5 ml, 0.25 mmol/5 ml, 1 mmol/15 ml. Coupling times and temperatures weregenerally 5 minutes at up to 70 or 75°C. Longer coupling times were used for larger scale reactions, for example 10min. Histidine amino acids were double coupled at 50°C, or quadruple coupled if the previous amino acid was stericallyhindered (e.g. Aib). Arginine amino acids were coupled at RT for 25 min then heated to 70 or 75°C for 5 min. Someamino acids such as but not limited to Aib, were "double coupled", meaning that after the first coupling (e.g. 5 min at75°C), the resin is drained and more reagents are added (amino acid, HOAt and DIC), and the mixture in heated again(e.g. 5 min at 75°C). When a chemical modification of a lysine side chain was desired, the lysine was incorporated asLys(Mtt). The Mtt group was removed by washing the resin with DCM and suspending the resin in neat (undiluted)hexafluoroisopropanol for 20 minutes followed by washing with DCM and NMP. The chemical modification of the lysinewas performed either by manual synthesis (see SPPS method D) or by one or more automated steps on the Libertypeptide synthesiser as described above, using suitably protected building blocks (see General methods), optionallyincluding a manual coupling. Preparation method: SPPS method B, starting with low-load Fmoc-Lys(Mtt)-Wang resin. Fmoc-Lys(Mtt)-OHwas used in position 26, and Boc-His(Trt)-OH was used in position 7. The Mtt was removed with HFIP, and 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid (commercially available from Iris Biotech), Fmoc-Glu-OtBu,and 4-(9-carboxy-nonyloxy)-benzoic acid tert-butyl ester (prepared as described in Example 25, step 2 of WO2006/082204) were coupled using a double coupling method on the Liberty Peptide synthesiser.UPLC (method 04_A3_1): 7.19 minLCMS4: m/z = 978.5 (M+5H)5+, 1222.8 (M+4H)4+ 1630.1 (M+3H)3+
  • 4
  • [ 159610-89-6 ]
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • C47H62N4O4 [ No CAS ]
  • [ 71989-31-6 ]
  • [ 198561-07-8 ]
  • [ 166108-71-0 ]
  • Fmoc-Glu(Pg)-OH [ No CAS ]
  • Fmoc-Lys(Pg)-OH [ No CAS ]
  • C120H189N27O30 [ No CAS ]
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