Structure of H-Lys(Boc)-OH
CAS No.: 2418-95-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: (S)-2-Amino-6-((tert-butoxycarbonyl)amino)hexanoic acid
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| CAS No. : | 2418-95-3 |
| Formula : | C11H22N2O4 |
| M.W : | 246.30 |
| SMILES Code : | O=C(O)[C@@H](N)CCCCNC(OC(C)(C)C)=O |
| Synonyms : |
(S)-2-Amino-6-((tert-butoxycarbonyl)amino)hexanoic acid
|
| MDL No. : | MFCD00037221 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
| Num. heavy atoms | 17 |
| Num. arom. heavy atoms | 0 |
| Fraction Csp3 | 0.82 |
| Num. rotatable bonds | 9 |
| Num. H-bond acceptors | 5.0 |
| Num. H-bond donors | 3.0 |
| Molar Refractivity | 63.98 |
| TPSA ? Topological Polar Surface Area: Calculated from |
101.65 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.96 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
-0.87 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.09 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
-1.61 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.29 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.17 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-0.22 |
| Solubility | 147.0 mg/ml ; 0.596 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-0.78 |
| Solubility | 40.6 mg/ml ; 0.165 mol/l |
| Class? Solubility class: Log S scale |
Very soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.52 |
| Solubility | 7.44 mg/ml ; 0.0302 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| 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 |
No |
| P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
| CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
| CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
| CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
| CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
| CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
| Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-8.42 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
| Ghose? Ghose filter: implemented from |
None |
| Veber? Veber (GSK) filter: implemented from |
0.0 |
| Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
| Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
| Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
| PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
| Brenk? Structural Alert: implemented from |
0.0 alert: heavy_metal |
| Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<2.0 |
| Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.71 |
* 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.

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| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 40% | The IBA-iRGD molecule was synthesized using standard solid phase synthesis protocols on a Fmoc-Cys(Trt)Wang Resin and Fmoc chemistry as described above. The following residues were coupled in order: Asp(OtBu), Pro, Gly, Lys(Boc), Asp(OtBu), Gly, Arg(Pbf), Cys(Trt), N-amido-dPEG2-acid, Lys(ivDde), N-amido-dPEG2-acid, Lys(Boc), mBA. The ivDde protecting group was removed by 2percent hydrazine in DMF. FITC was allowed to react for 3 h in DMF. The molecule was then cleaved from the resin in 92.5percent TFA, 2.5percent TIS, 2.5percent EDT and 2.5percent DI. water, purified via RP-HPLC on a Zorbax C18 column, and characterized using MALDI-TOF MS (FIG. 13). The peptide was cyclized overnight in DMF with DIEA and cyclization was verified via MALDI-TOF MS. The yield was 40percent, and product purity was confirmed using RP-HPLC on an analytical Zorbax C18 colunm to be >95percent. |
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| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| H2N-L-Cys(Trt)-D-Leu-L-Trp(Boc)-D-Leu-L-Lys(Boc)-D-Leu-L-Trp(Boc)-D-Leu-COOH. Fully protected linear octapeptide was prepared via solid phase peptide synthesis (SPPS) on a Prelude Automated Peptide SynthesizerTM (Protein Technologies Inc.) using 2-ch lorotrityl chloride resin as the solid support. The first Fmoc protected amino acid was coupled to the resin using DIPEA (4 eq.) in DCM, followed by capping of unreacted resin sites using a solution of MeOH : DIPEA: DCM (7: 1 :2, v/v/v). Deprotection of the Fmoc group of the amino acids was done using 20percent piperidine in DMF. Subsequent amino acids were coupled using Fmoc-amino acids (5 eq.), HCTU (5 eq.) and NMM (10 eq.) in DMF. In the last step, the linear octapeptide was cleaved from the resin (while keeping protecting groups on) by a solution of 20 vol percent l, l,l,3,3,3-hexafluoro-2-propanol (HFIP) in DCM. MS (ESI-ToF) (m/z) : [M + H]+ 1616.9 (calculated : 1616.9). |