143824-78-6|Fmoc-L-Trp(Boc)-OH| Ambeed

Structure of Fmoc-Trp(Boc)-OH
CAS No.: 143824-78-6

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Synonyms: Fmoc-L-Trp(Boc)-OH

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Quality Control of [ 143824-78-6 ] Purity: 98% （contains~6.0% PE） SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Citations

Non-Invasive Ultrasonic Debridement of Implant Biofilms Via Hydrogen-Sulfide Releasing Peptide Nanoemulsions

Singh, Harminder ; Biswas, Diptomit ; Medina, Scott ;

DOI: 10.2139/ssrn.5044770 Pennsylvania State University,2024.

Abstract: Implant contamination by bacterial biofilms remains a significant healthcare burden, often necessitating revision surgeries due to biofilm-enabled antibiotic resistance. Physical debridement, in combination with chemical antiseptics, is a simple and effective therapeutic strategy, but requires highly invasive surgical procedures and risks secondary infection events. Herein, we report a non-invasive, nanoparticle-enabled ultrasonic debridement strategy that exerts synergistic physical and chemical antiseptic effects to rapidly and efficiently clear implant-associated biofilms in situ. This approach is realized through the development of hydrogen sulfide- releasing peptide nanoemulsions that preferentially target bacterial biofilms and can be vaporized via diagnostic ultrasound to spatiotemporally clear methicillin-resistant Staphylococcus aureus (MRSA) infections. Biophysical studies elucidate the mechanistic basis for the platform’s antibiofilm activity, and in vitro and ex vivo experiments confirm efficacy in the context of MRSA-infected titanium implants. By exploiting the portable, low cost and safe nature of low intensity diagnostic ultrasound, this non-invasive approach avoids the collateral tissue damage associated with current surgical and high intensity acoustic ablative modalities.

Purchased from AmBeed: 154445-77-9 ; 143824-78-6

Product Details of [ 143824-78-6 ]

CAS No. :	143824-78-6
Formula :	C₃₁H₃₀N₂O₆
M.W :	526.57
SMILES Code :	O=C(O)[C@H](CC1=CN(C(OC(C)(C)C)=O)C2=CC=CC=C12)NC(OCC3C4=C(C5=C3C=CC=C5)C=CC=C4)=O
Synonyms :	Fmoc-L-Trp(Boc)-OH
MDL No. :	MFCD00153366
InChI Key :	ADOHASQZJSJZBT-SANMLTNESA-N
Pubchem ID :	9849766

Safety of [ 143824-78-6 ]

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

Computational Chemistry of [ 143824-78-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	39
Num. arom. heavy atoms	21
Fraction Csp3	0.26
Num. rotatable bonds	11
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	147.36
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	106.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.67
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	5.99
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	5.96
Log P_o/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.	3.96
Log P_o/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	4.48
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	4.81

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-6.55
Solubility	0.000148 mg/ml ; 0.000000281 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Poorly soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-8.01
Solubility	0.00000513 mg/ml ; 0.0000000098 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	-8.2
Solubility	0.00000335 mg/ml ; 0.0000000064 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	Low
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) 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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.26 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	1.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	1.0
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	1.0 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<3.0
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)	4.55

Application In Synthesis of [ 143824-78-6 ]

* 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 [ 143824-78-6 ]

[ 143824-78-6 ] Synthesis Path-Downstream 1~54

1
[ 108-24-7 ]
[ 91000-69-0 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Ac-His-Nal(1')-Arg-Trp-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3073 - 3081.

2
[ 811434-05-6 ]
[ 124-07-2 ]
Fmoc-Thr(Bzl)-O-HMP-resin [ No CAS ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
[ 143824-78-6 ]
C₁₁₄H₁₃₄Cl₅N₁₇O₂₄ [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 240 - 244.

3
[ 811434-05-6 ]
C₂₆H₂₄NO₅Pol [ No CAS ]
[ 35661-60-0 ]
[ 86123-10-6 ]
[ 125238-99-5 ]
[ 117872-75-0 ]
[ 143824-78-6 ]
[ 1173986-45-2 ]

References: [1]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 332 - 336.

4
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 96402-49-2 ]
[ 143824-78-6 ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₆₁H₇₆N₁₀O₁₀S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3927 - 3940.

5
C₂₇H₃₁ClNO₂Pol [ No CAS ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 86123-10-6 ]
[ 96402-49-2 ]
[ 146549-21-5 ]
[ 143824-78-6 ]
[ 1241047-38-0 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 6188 - 6197.

6
C₂₇H₃₁ClNO₂Pol [ No CAS ]
[ 71989-26-9 ]
[ 71989-40-7 ]
[ 86123-10-6 ]
[ 96402-49-2 ]
[ 146549-21-5 ]
[ 143824-78-6 ]
[ 1241047-41-5 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 6188 - 6197.

7
[ 4497-04-5 ]
C₄₂H₄₁N₄O₈Pol [ No CAS ]
[ 143824-78-6 ]
[ 1241875-27-3 ]

References: [1]Journal of Combinatorial Chemistry,2010,vol. 12,p. 676 - 686.

8
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
H-(propargylglycyl)-QGTFTSDYSKYLDSRRAQDFVQWLMNTKRNRNNIA-NH₂ [ No CAS ]

References: [1]Journal of Peptide Science,2011,vol. 17,p. 270 - 280.

9
[ 35661-39-3 ]
C₂₉H₃₀N₇O₄Pol [ No CAS ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 32926-43-5 ]
[ 143824-78-6 ]
C₇₉H₉₀N₁₅O₁₂Pol [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 3588 - 3591.

10
[ 35661-39-3 ]
C₃₁H₃₆N₅O₄Pol [ No CAS ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 32926-43-5 ]
[ 143824-78-6 ]
[ 1615698-10-6 ]

References: [1]Organic Letters,2014,vol. 16,p. 3588 - 3591.

11
[ 35661-39-3 ]
C₃₅H₄₂N₅O₆Pol [ No CAS ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 32926-43-5 ]
[ 143824-78-6 ]
[ 1615698-09-3 ]

References: [1]Organic Letters,2014,vol. 16,p. 3588 - 3591.

12
[ 64-18-6 ]
[ 35661-39-3 ]
C₃₂H₃₉N₅O₄Pol⁽¹⁺⁾ [ No CAS ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
[ 32926-43-5 ]
[ 143824-78-6 ]
[ 1615698-12-8 ]

References: [1]Organic Letters,2014,vol. 16,p. 3588 - 3591.

13
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 96402-49-2 ]
[ 143824-78-6 ]
Fmoc-[β-dimethylcysteine](Trt)-OH [ No CAS ]
C₅₆H₇₂N₁₀O₁₁S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5965 - 5974.

14
[ 159610-89-6 ]
[ 108-24-7 ]
[ 86123-10-6 ]
[ 109425-51-6 ]
[ 77284-32-3 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
Ac-Nle-Pra-His-D-Phe-Arg-Trp-Nle(ε-N_3)-NH2 [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9424 - 9434.

15
[ 159610-89-6 ]
[ 108-24-7 ]
[ 86123-10-6 ]
[ 109425-51-6 ]
[ 77284-32-3 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
Ac-Nle-Nle(N3)-His-D-Phe-Arg-Trp-Pra-NH2 [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 9424 - 9434.

16
C₂₃H₂₂NO₆Pol [ No CAS ]
C₁₇H₃₅NO₅Si [ No CAS ]
[ 35661-60-0 ]
[ 132327-80-1 ]
[ 77128-73-5 ]
[ 71989-33-8 ]
[ 56-40-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
N-FMOC-O-tert-butyl-D-threonine [ No CAS ]
Fmoc-D-Ile-OH [ No CAS ]
C₇₅H₁₁₆N₂₀O₂₀ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 1556 - 1560.
Angew. Chem.,2015,vol. 127,p. 1576 - 1580,5.

17
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGA-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314.

18
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGF-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314.

19
[ 35661-60-0 ]
[ 35661-51-9 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 108-24-7 ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Ac-Tyr-Asn-Trp-Asn-Ser-Phe-azaGly-Leu-Arg-Tyr-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3459 - 3470.

20
fmoc-Phe-Alko Resin [ No CAS ]
[ 29022-11-5 ]
[ 143824-78-6 ]
[ 198561-07-8 ]
C₄₂H₃₉N₅O₇ [ No CAS ]

References: [1]New Journal of Chemistry,2015,vol. 39,p. 4534 - 4550.

21
H-Trp(Boc)-2-chlorotrityl chloride resin [ No CAS ]
[ 143824-78-6 ]
[ 198561-07-8 ]
C₆₀H₅₇N₁₁O₇ [ No CAS ]

References: [1]ChemMedChem,2014,vol. 9,p. 2449 - 2453.

22
H-Trp(Boc)-2-chlorotrityl chloride resin [ No CAS ]
[ 143824-78-6 ]
[ 198561-07-8 ]
C₈₅H₉₇N₁₁O₁₇ [ No CAS ]

References: [1]ChemMedChem,2014,vol. 9,p. 2449 - 2453.

23
polyethylene glycol polyamide resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
Palm-γGlu-γGlu-OSu [ No CAS ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132327-80-1 ]
[ 71989-33-8 ]
[ 94744-50-0 ]
[ 32926-43-5 ]
[ 143824-78-6 ]
[ 204777-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
H-dSer-Q-G-T-F-T-S-D-L-S-K-Q-K((S)-4-carboxy-4-((S)-4-carboxy-4-hexadecanoylamino-butyrylamino)butyryl)-D-E-E-A-A-R-L-F-I-E-W-L-Aib-A-G-G-P-S-S-G-A-P-P-P-S-NH₂ [ No CAS ]