73724-45-5|Fmoc-Ser-OH| Ambeed

Structure of Fmoc-Ser-OH
CAS No.: 73724-45-5

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Quality Control of [ 73724-45-5 ] Purity: 98% SDS Specification

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Product Citations

Probing the Effects of Chirality on Self-Assembling Peptides: Hydrogel Formation, Degradation, Antigen Release, and Adjuvancy

Agrawal, Anushka ; Euliano, Erin M ; Pogostin, Brett H ; Yu, Marina H ; Swain, Joseph WR ; Hartgerink, Jeffrey D , et al.

DOI: 10.1007/s12195-024-00806-1 Cel. Mol. Bioeng.,2024,17,441-451.

Abstract: Introduction Multidomain peptides (MDPs) are amino acid sequences that self-assemble to form supramolecular hydrogels under physiological conditions that have shown promise for a number of biomedical applications. K₂(SL)₆K₂ (“K₂”), a widely studied MDP, has demonstrated the ability to enhance the humoral immune response to co-delivered antigen. Herein, we sought to explore the in vitro and in vivo properties of a peptide with the same sequence but opposite chirality (D-K₂) since peptides composed of D-amino acids are resistant to protease degradation and potentially more immunostimulatory than their canonical counterparts. Methods K₂ and D-K₂ hydrogels were characterized and evaluated in vitro using circular dichroism, rheology, cryo-electron microscopy, and fuorescence recovery after photobleaching studies. In vivo experiments in SKH-1 mice were conducted to evaluate both ovalbumin release from the hydrogels and hydrogel degradation. The injection site of the hydrogels was analyzed using histology and humoral immunity was assessed by ELISA. Results In vitro, the enantiomeric hydrogels exhibited similar rheological properties, and fuorescence recovery after pho_x005f_x0002_tobleaching experiments demonstrated that the difusion of ovalbumin (OVA), a model antigen, was similar within both hydrogels. In vivo, K₂ and D-K₂ peptide hydrogels had similar OVA release rates, both releasing 89% of the antigen within 8 days. Both hydrogels elicited a similar antigen-specifc humoral immune response. However, the in vivo degradation of the D-K₂ hydrogel progressed signifcantly slower than K₂. After 4 weeks in vivo, only 23±7% of the K₂ hydrogel remained at the injection site compared to 94±7% of the D-K₂ hydrogel, likely due to their diferent protease susceptibilities. Conclusion Taken together, these data suggest that peptide chirality can be a useful tool for increasing hydrogel residence time for biomedical applications that would beneft from long persistence times and that, if an antigen releases over a suf_x005f_x0002_fciently short period, release can be largely independent of degradation rate, though slower-difusing payloads may exhibit degradation rate dependence.

Keywords: Hydrogel ; Chirality ; Degradation ; Drug delivery ; Peptides ; Adjuvants

Purchased from AmBeed: 73724-45-5 ; 35661-60-0 ; 114360-54-2 ; 110990-08-4 ; 116861-26-8

Product Details of [ 73724-45-5 ]

CAS No. :	73724-45-5
Formula :	C₁₈H₁₇NO₅
M.W :	327.33
SMILES Code :	OC[C@@H](C(O)=O)NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O
MDL No. :	MFCD00051928

Safety of [ 73724-45-5 ]

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

Computational Chemistry of [ 73724-45-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	24
Num. arom. heavy atoms	12
Fraction Csp3	0.22
Num. rotatable bonds	7
Num. H-bond acceptors	5.0
Num. H-bond donors	3.0
Molar Refractivity	86.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	95.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.0
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	2.0
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.97
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.	1.51
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	1.93
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.88

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.04
Solubility	0.3 mg/ml ; 0.000917 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.64
Solubility	0.075 mg/ml ; 0.000229 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-4.33
Solubility	0.0153 mg/ml ; 0.0000469 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	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	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	No
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	No
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.	-6.88 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	0.0
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	0.0
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<0.0
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)	3.7

Application In Synthesis of [ 73724-45-5 ]

* 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 [ 73724-45-5 ]

[ 73724-45-5 ] Synthesis Path-Downstream 1~41

1
[ 29022-11-5 ]
[ 108-24-7 ]
[ 73724-45-5 ]
[ 77128-73-5 ]
(S)-2-[((S)-2-Acetylamino-3-hydroxy-propionyl)-methyl-amino]-N-[(carbamoylmethyl-carbamoyl)-methyl]-3-phenyl-propionamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 103 - 113.

2
[ 6214-20-6 ]
[ 108-24-7 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 77128-73-5 ]
Fmoc-Val [ No CAS ]
Ac-Val-NMeGln-Ser-NMePhe-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 103 - 113.

3
[ 159610-89-6 ]
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-32-4 ]

References: [1]European Journal of Organic Chemistry,2010,p. 446 - 457.

4
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 1097192-04-5 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-30-2 ]

References: [1]European Journal of Organic Chemistry,2010,p. 446 - 457.

5
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 1097192-04-5 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-28-8 ]

References: [1]European Journal of Organic Chemistry,2010,p. 446 - 457.

6
[ 918663-78-2 ]
C₃₆H₃₄N₄O₆ [ No CAS ]
[ 73724-45-5 ]
[ 96402-49-2 ]
[ 1187754-71-7 ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7836 - 7846.

7
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 67436-13-9 ]
[ 73724-45-5 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Fmoc-Lys(Boc)-OH [ No CAS ]
Fmoc-Glu(OtBu)-OH [ No CAS ]
Fmoc-Met-OH [ No CAS ]
acetic anhydride [ No CAS ]
Ac-(cyclo 1-20)-CPEMREKLSGHHFVRALARCSGGPR(1Nal)-NH₂ [ No CAS ]

References: [1]Amino Acids,2010,vol. 38,p. 121 - 131.

8
Fmoc-Ala-O-Wang resin [ No CAS ]
[ 124-07-2 ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-39-3 ]
[ 35661-40-6 ]
[ 118904-37-3 ]
[ 71989-18-9 ]
[ 73724-45-5 ]
[ 125238-99-5 ]
[ 84624-17-9 ]
N-α-(9-fluorenylmethyloxycarbonyl)-N-γ-tert-butyloxycarbonyl-D-2,4-diaminobutyric acid [ No CAS ]
Protected D-Trp derivative [ No CAS ]
[ 1628113-77-8 ]