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Chemical Structure| 27144-18-9 Chemical Structure| 27144-18-9

Structure of 3-(Tritylthio)propionic acid
CAS No.: 27144-18-9

Chemical Structure| 27144-18-9

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Product Details of [ 27144-18-9 ]

CAS No. :27144-18-9
Formula : C22H20O2S
M.W : 348.46
SMILES Code : O=C(O)CCSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
MDL No. :MFCD00237291
InChI Key :AECGEIVNZGQBJT-UHFFFAOYSA-N
Pubchem ID :262767

Safety of [ 27144-18-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335-H413
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 27144-18-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 18
Fraction Csp3 0.14
Num. rotatable bonds 7
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 104.05
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

62.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.89
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

5.05
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

5.08
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

4.81
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

5.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.6

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.25
Solubility 0.00195 mg/ml ; 0.00000559 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-6.11
Solubility 0.000273 mg/ml ; 0.000000783 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-7.74
Solubility 0.00000641 mg/ml ; 0.0000000184 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

Yes
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

Yes
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.84 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

1.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

3.27

Application In Synthesis of [ 27144-18-9 ]

* 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 [ 27144-18-9 ]

[ 27144-18-9 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 27144-18-9 ]
  • [ 625-51-4 ]
  • [ 52574-08-0 ]
  • 2
  • 2-chlorotrityl chloride polystyrene resin [ No CAS ]
  • [ 162502-65-0 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 71989-31-6 ]
  • [ 71989-23-6 ]
  • [ 71989-35-0 ]
  • [ 132388-59-1 ]
  • [ 86060-81-3 ]
  • [ 109425-55-0 ]
  • C93H116N11O16PolS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Synthesis of the peptide is carried out by a regular stepwise Fmoc SPPS procedure starting from 2-Cl-Trt-chloride resin. The first amino acid (Fmoc-Gly) is loaded on the resin as described in previous examples to obtain a loading of about 0.7 mmol/g of amino acid/resin. After washing of the resin and removal of the Fmoc group by treatment with piperidine/DMF, the second amino acid (Fmoc-Orn(Boc)) is introduced to continue sequence elongation. Fmoc protected amino acids are activated in situ using TBTU/HOBt and subsequently coupled to the resin over about 50 minutes. Diisopropylethylamine or collidine is used during coupling as an organic base. Completion of the coupling is indicated by ninhydrin test. After washing of the resin, the Fmoc protecting group on the alpha-amine is removed with 20% piperidine in DMF for 20 min. These steps are repeated each time with another amino acid according to the peptide sequence. All amino acids used are Fmoc-Nalpha protected. Trifunctional amino acids are side chain protected as follows: Cys(Acm), Thr(tBu), Asn(Trt), and Orn(Boc). Three equivalents of the activated amino acids are used in the coupling reactions. At the end of the synthesis, the peptide-resin is washed with DMF, followed by DCM, and dried under vacuum to obtain dry peptide-resin.
  • 3
  • [ 4530-20-5 ]
  • [ 13139-16-7 ]
  • [ 13139-15-6 ]
  • [ 15761-38-3 ]
  • [ 2488-15-5 ]
  • [ 7536-55-2 ]
  • [ 19746-37-3 ]
  • [ 27144-18-9 ]
  • [ 13734-34-4 ]
  • [ 23680-31-1 ]
  • [ 55260-24-7 ]
  • mouse saposin C [ No CAS ]
  • 4
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 15761-38-3 ]
  • [ 27144-18-9 ]
  • [ 13734-34-4 ]
  • [ 15260-10-3 ]
  • [ 13574-13-5 ]
  • [ 13836-37-8 ]
  • [ 65420-40-8 ]
  • [ 55260-24-7 ]
  • [ 35899-43-5 ]
  • H-LQIFVKTLTGKTITLEVEPSDTIENVK-SCH2CH2CONH2 [ No CAS ]
  • 5
  • [ 4530-20-5 ]
  • [ 15761-39-4 ]
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 13139-15-6 ]
  • [ 27144-18-9 ]
  • [ 15260-10-3 ]
  • [ 23680-31-1 ]
  • [ 61925-77-7 ]
  • [ 54613-99-9 ]
  • [ 47355-10-2 ]
  • cycloCGETCVGGTCNTPGCTCSWPVCQIPGLGPL cyclic (1->15),(5->17),(10->22)-tris(disulfide) [ No CAS ]
  • 6
  • [ 4530-20-5 ]
  • [ 13139-15-6 ]
  • [ 27144-18-9 ]
  • [ 18942-46-6 ]
  • [ 54613-99-9 ]
  • [ 47689-67-8 ]
  • [ 47355-10-2 ]
  • C46H63N11O11S3 [ No CAS ]
  • 7
  • [ 4530-20-5 ]
  • Boc-Gly-PAM resin [ No CAS ]
  • [ 13139-15-6 ]
  • [ 27144-18-9 ]
  • [ 18942-46-6 ]
  • [ 54613-99-9 ]
  • [ 47689-67-8 ]
  • [ 47355-10-2 ]
  • C40H66N10O10S3 [ No CAS ]
  • 8
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-39-3 ]
  • C36H30NO3Pol [ No CAS ]
  • [ 35661-40-6 ]
  • [ 92122-45-7 ]
  • [ 35661-38-2 ]
  • [ 71989-33-8 ]
  • [ 104091-08-9 ]
  • Fmoc-protected derivatives of D-His and Met [ No CAS ]
  • SHC<SUB>2</SUB>H<SUB>4</SUB>CO-D-Ser-Met-D-Glu-Val-D-Ala-Gly-D-Lys-Ala-D-His-Phe-Gly-Gly-NHC<SUB>2</SUB>H<SUB>4</SUB>OH [ No CAS ]
  • 9
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • C36H30NO3Pol [ No CAS ]
  • [ 35661-40-6 ]
  • [ 92122-45-7 ]
  • [ 71989-23-6 ]
  • [ 35661-38-2 ]
  • [ 104091-08-9 ]
  • SHC<SUB>2</SUB>H<SUB>4</SUB>CO-D-Ala-Ile-D-Lys-Phe-D-Ala-Gly-D-Lys-Ala-D-Glu-Ile-D-Lys-Ala-NHC<SUB>2</SUB>H<SUB>4</SUB>OH [ No CAS ]
  • 10
  • [ 4530-20-5 ]
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 15761-38-3 ]
  • [ 27144-18-9 ]
  • C9H15NO5 [ No CAS ]
  • [ 20887-95-0 ]
  • [ 47689-67-8 ]
  • [ 65420-40-8 ]
  • [ 55260-24-7 ]
  • C58H92N16O19S3 [ No CAS ]
  • 11
  • [ 4530-20-5 ]
  • [ 13734-41-3 ]
  • [ 13139-16-7 ]
  • [ 15761-38-3 ]
  • [ 27144-18-9 ]
  • C9H15NO5 [ No CAS ]
  • [ 47689-67-8 ]
  • [ 65420-40-8 ]
  • [ 55260-24-7 ]
  • [ 1610353-03-1 ]
  • 12
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 35661-60-0 ]
  • [ 147290-11-7 ]
  • C55H78N13O12PolS [ No CAS ]
  • 13
  • [ 4530-20-5 ]
  • [ 15761-39-4 ]
  • [ 13734-41-3 ]
  • [ 13139-15-6 ]
  • [ 15761-38-3 ]
  • [ 7536-58-5 ]
  • [ 13726-85-7 ]
  • [ 27144-18-9 ]
  • [ 13574-13-5 ]
  • [ 23680-31-1 ]
  • [ 54613-99-9 ]
  • [ 51077-16-8 ]
  • [ 47355-10-2 ]
  • [ 25024-53-7 ]
  • Boc-R(PG)-OH [ No CAS ]
  • C155H252N41O43PolS2 [ No CAS ]
  • 14
  • [ 4530-20-5 ]
  • [ 13734-41-3 ]
  • [ 13139-15-6 ]
  • [ 15761-38-3 ]
  • [ 2488-15-5 ]
  • [ 13726-85-7 ]
  • [ 27144-18-9 ]
  • [ 13574-13-5 ]
  • [ 54613-99-9 ]
  • [ 51077-16-8 ]
  • [ 47355-10-2 ]
  • Boc-R(PG)-OH [ No CAS ]
  • C99H150N27O26PolS3 [ No CAS ]
  • 15
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 112883-29-1 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C61H75F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g-1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. (0835) The sequence of Fmoc protected amino acids and building blocks used are: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine (0836) 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid (0837) 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine (0838) 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine (0839) 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (0840) 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid (0841) 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid (0842) 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine (0843) 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine (0844) 10.3-(tritylthio)propanoic acid (0845) At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS anal calcd. C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1 )+
  • 16
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • [ 35661-38-2 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C63H79F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g-1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M L/,/V-diisopropylcarbodiimide (DIC) (double coupling for Y01 ). Fmoc deprotection cycles were performed using 20% (VA/) piperidine in DMF. (0856) The sequence of Fmoc protected amino acids and building blocks used are: (0857) 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2 -carboxylic acid (0858) 3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid (0859) 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine (0860) 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid (0861) 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid (0862) 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid (0863) 8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine (0864) 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine (0865) 10.3-(tritylthio)propanoic acid (0866) At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. (0867) LCMS anal calcd. C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1 )+
  • 17
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine [ No CAS ]
  • [ 112883-29-1 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C61H75F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. (0284) The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS analysis was calculated for C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1)+
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/iBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. (0775) The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H20, 4% TIPS) for approximately 1 .5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS analysis was calculated for C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1 )+
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et2
  • 18
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine [ No CAS ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • [ 35661-38-2 ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C63H79F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M A/,//-diisopropylcarbodiimide (DIC) (double coupling for Y01). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et2 H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. LCMS analysis was calculated for C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1)+.
  • 19
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 112883-29-1 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C61H75F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 0.5M HATU in DMF, 4eq of 2M DIPEA (double coupling for Tyr). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were:1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid3. (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tyrosine4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3-yl)propanoic acid8. (((9H-fluoren-9-yl)methoxy)carbonyl)glycine9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine10. 3-(tritylthio)propanoic acidAt the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5%H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (399mg), which was used as crude in the next step. LCMS analysis was calculated for C61 H75F2N15013S2: 1328.48, found: 1328.2 (M+1)+
  • 20
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • [ 29022-11-5 ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • 9-fluorenylmethoxycarbonyl-Nim-trityl-L-histidine [ No CAS ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • C63H79F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M A/,//-diisopropylcarbodiimide (DIC)(double coupling for Y01). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF.The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine2. (S)-1((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine10. 3-(tritylthio)propanoic acidAt the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5%H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. LCMS analysis was calculated for C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1)+.
  • 21
  • [ 908846-88-8 ]
  • [ 27144-18-9 ]
  • N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine [ No CAS ]
  • [ 71989-14-5 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • [ 35661-38-2 ]
  • [ 77128-72-4 ]
  • (S)-1-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 76-05-1 ]
  • C63H79F2N15O13S2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/iBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M A/,A/-diisopropylcarbodiimide (DIC) (double coupling for Y01 ). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H20, 4% TIPS) for approximately 1 .5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. LCMS analysis was calculated for C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1 )+.
The peptide was synthesized on a 0.250 mmol scale on CEM Liberty Blue, Microwave synthesizer using Fmoc/fBu chemistry on PS Rink-Amide MBHA resin, 0.32 mmol g_1. The assembly was performed using single-couplings using 4eq of Fmoc protected amino acid 0.2M in DMF, 4eq of 1 M Oxyme in DMF, 4eq of 0.5M A/,//-diisopropylcarbodiimide (DIC) (double coupling for Y01). Fmoc deprotection cycles were performed using 20% (V/V) piperidine in DMF. The sequence of Fmoc protected amino acids and building blocks used were: 1. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-S-trityl-L-cysteine 2. (S)-1 ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpyrrolidine-2-carboxylic acid 3. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-methoxyphenyl)propanoic acid 4. N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-trityl-L-histidine 5. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-(tert-butoxy)-4-oxobutanoic acid 6. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 7. (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(5-fluoro-1 H-indol-3- yl)propanoic acid 8. (((9H-fluoren-9-yl)methoxy)carbonyl)-D-alanine 9. N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(tert-butoxycarbonyl)-L-lysine 10. 3-(tritylthio)propanoic acid At the end of the assembly, the resin was washed with DMF, MeOH, DCM, Et20. The peptide was cleaved from solid support using 50 ml of TFA solution (v/v) (91 % TFA, 5% H2O, 4% TIPS) for approximately 1.5 hours, at room temperature. The resin was filtered, washed with TFA and solution concentrated to dryness and lyophilized. Lyophilization afforded Intermediate Compound Int. A (300mg), which was used as crude in the next step. LCMS analysis was calculated for C63H79F2N15013S2: 1356.53, found: 1356.9 (M+1 )+.
 

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