Fmoc-Glu(OtBu)-OH | (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid | Carboxylic Acids

Structure of Fmoc-Glu(OtBu)-OH
CAS No.: 71989-18-9

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Synonyms: (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid

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Quality Control of [ 71989-18-9 ] Purity: 98% contains ~4% water SDS Specification

COA

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CNMR

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Product Citations Show More

Potent Cyclic Peptide Inhibitors Disrupt the FANCM–RMI Interaction

Alcock, Lisa J ; Gao, Tianyi ; Bythell-Douglas, Rohan ; Gao, Jixuan ; Krishna Sudhakar, Haritha ; Huang, Tiancheng , et al.

DOI: 10.1021/acs.jmedchem.5c00365 PubMed ID: 40479515 JMC,2025,68(12):12615-12625.

Abstract: FANCM−RMI is a protein−protein interaction that maintains genome stability during DNA repair events in cancers that rely on the Alternative Lengthening of Telomeres (ALT) pathway for survival. We report the first valid chemical inhibitors of the FANCM−RMI interaction discovered by screening cyclic peptides via mRNA display. These inhibitors engage the FANCM-binding pocket of RMI1/2 with nanomolar affinity (K_D = 2−10 nM) and are potent disruptors of the FANCM−RMI interaction (IC₅₀ = 54−104 nM). X-ray crystallography and alanine scanning reveal novel binding modes and interactions between the cyclic peptides and RMI1/2 that drive high-potency inhibition. Co-immunoprecipitation studies confirm the complete disruption of the native interaction in whole osteosarcoma cell lysates. These inhibitors represent the first validated RMI binders toward developing chemical tools for interrogating the mechanistic roles of FANCM−RMI in mediating genome stability and provide a much-anticipated starting point to accelerate the development of FANCM−RMI inhibitors for intervention against ALT-driven cancers.

Purchased from AmBeed: 71989-18-9

Differences in the Renal Accumulation of Radiogallium-Labeled (Glu) 14 Peptides Containing Different Optical Isomers of Glutamic Acid

Ogawa, Kazuma ; Nishizawa, Kota ; Mishiro, Kenji ; Munekane, Masayuki ; Fuchigami, Takeshi ; Echigo, Hiroaki , et al.

DOI: 10.3390/molecules29173993 Molecules,2024,29(17):3993.

Abstract: Acidic amino acid peptides have a high affinity for bone. Previously, we demonstrated that radiogallium complex-conjugated oligo-acidic amino acids possess promising properties as bone-seeking radiopharmaceuticals. Here, to elucidate the effect of stereoisomers of Glu in Glu-containing peptides [(Glu)₁₄] on their accumulation in the kidney, the biodistributions of [⁶⁷Ga]Ga-N,N′ -bis-[2-hydroxy- 5-(carboxyethyl)benzyl]ethylenediamine-N,N′ -diacetic acid-conjugated (L-Glu)₁₄ ([⁶⁷Ga]Ga-HBED-CC- (L-Glu)₁₄), [⁶⁷Ga]Ga-HBED-CC-(D-Glu)₁₄, [⁶⁷Ga]Ga-HBED-CC-(DL-Glu)₁₄, and [⁶⁷Ga]Ga-HBED-CC- (D-Glu-L-Glu)₇ were compared. Although the accumulation of these compounds in the bone was comparable, their kidney accumulation and retention were strikingly different, with [⁶⁷Ga]Ga-HBED-CC- (D-Glu-L-Glu)₇ exhibiting the lowest level of kidney accumulation among these compounds. Repeated D- and L-peptides may be a useful method for reducing renal accumulation in some cases.

Keywords: kidney accumulation ; bone imaging ; glutamic acid ; bone metastases ; gallium

Purchased from AmBeed: 71989-18-9 ; 104091-08-9

Product Details of [ 71989-18-9 ]

CAS No. :	71989-18-9
Formula :	C₂₄H₂₇NO₆
M.W :	425.47
SMILES Code :	O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CCC(OC(C)(C)C)=O
Synonyms :	(S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid
MDL No. :	MFCD00037135
InChI Key :	OTKXCALUHMPIGM-FQEVSTJZSA-N
Pubchem ID :	2724637

Safety of [ 71989-18-9 ]

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

Computational Chemistry of [ 71989-18-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	31
Num. arom. heavy atoms	12
Fraction Csp3	0.38
Num. rotatable bonds	11
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	115.34
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	101.93 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	3.19
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	3.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.1
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.	2.77
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	3.74
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.53

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.46
Solubility	0.0146 mg/ml ; 0.0000344 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.	-5.69
Solubility	0.000875 mg/ml ; 0.00000206 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-6.13
Solubility	0.000314 mg/ml ; 0.000000738 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	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	Yes
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	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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.16 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	1.0
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	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)	4.35

Application In Synthesis of [ 71989-18-9 ]

* 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 [ 71989-18-9 ]

[ 71989-18-9 ] Synthesis Path-Downstream 1~41

1
[ 122889-11-6 ]
[ 71989-18-9 ]
[ 35737-15-6 ]
[ 35661-38-2 ]
Cbz-His-OH [ No CAS ]
(R)-4-{(R)-2-Benzyloxy-1-[(R)-1-((S)-1-carbamoyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-ethylcarbamoyl}-4-[(R)-2-benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-butyric acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 192 - 200.

2
[ 71989-18-9 ]
Fmoc-Leu-OH [ No CAS ]
[ 145038-49-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2795 - 2798.

3
C₃₄H₂₈N₂O₇ [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 103213-32-7 ]
[ 86060-81-3 ]
[ 116611-64-4 ]
[ 223416-45-3 ]

Yield	Reaction Conditions	Operation in experiment
		Chelmical synthesis: Peptides were synthesized on a Rink amide resin, 0.45 mmol/g [Fmoc-Cys(Trityl)-Wang; Novabiochem, San Diego, Calif.] usinig N-(9-fluorenyl)methoxycarboxyl chemistry and standard side chain protection except on cysteine residues. Cysteine residues were protected in pairs with either S-trityl on the first and third cysteines or S-acetamidomethyl on the second and fourth cysteines. Amino acid derivatives were from Advanced Chemtech (Louisville, Ky.). The peptides were removed from the resin and precipitated, and a two-step oxidation protocol was used to selectively fold the peptides as described previously (Luo et al., 1999). Briefly, the first disulfide bridge was closed by dripping the peptide into an equal volume of 20 mM potassium feliicyanide and 0.1 M Tris, pH 7.5. The solution was allowed to react for 30 min, and the monocyclic peptide was purified by reverse-phase HPLC. Simultaneous removal of the S-acetamidomethyl groups and closure of the second disulfide bridge was carried out by iodine oxidation. The monocyclic peptide and HPLC eluent was dripped into an equal volume of iodine (10 mM) in H20/trifluoroacetic acid/acetonitrile (78:2:20 by volume) and allowed to react for 10 min. The reaction was terminated by the addition of ascorbic acid diluted 20-fold with 0.1percent trifluoroacetic acid and the bicyclic product purified by HPLC. Mass Spectrometry: Measurements were performed at the Salk Institute for Biological Studies (San Diego, Calif.) under the direction of Jean Rivier. Matrix-assisted laser desorption ionization time-of-flight mass spectrometry and liquid secondary ionization mass spectrometry were used.

References: [1]Patent: US2006/211623,2006,A1 .Location in patent: Page/Page column 9.

4
[ 35661-40-6 ]
[ 71989-18-9 ]
[ 125238-99-5 ]
[ 135673-97-1 ]
N-[(9-fluorenyl)methoxycarbonyl]-4-chloro-L-phenylalanine [ No CAS ]
[ 1186310-44-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237.

5
[ 71989-18-9 ]
[ 132684-59-4 ]
[ 77284-32-3 ]
[ 135112-28-6 ]
[ 125238-99-5 ]
N-(9-fluorenylmethoxycarbonyl)-3-(β-naphthyl)-L-alanine [ No CAS ]
[ 1349220-85-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 5229 - 5237.

6
C₃₃H₃₄N₃O₅Pol [ No CAS ]
[ 29022-11-5 ]
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-35-0 ]
[ 109425-51-6 ]
His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Ser(OBn)-[2-amino-3-(biphenyl-4-yl)propanoyl]-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7788 - 7799.

7
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 71989-16-7 ]
[ 91000-69-0 ]
[ 198561-07-8 ]
C₅₇H₉₃N₁₇O₂₂ [ No CAS ]

References: [1]Organic Letters,2011,vol. 13,p. 5604 - 5607.

8
[ 35661-39-3 ]
[ 1356004-85-7 ]
[ 71989-18-9 ]
[ 71989-26-9 ]
[ 198561-07-8 ]
[ 1421510-90-8 ]

References: [1]Chemical Communications,2013,vol. 49,p. 4540 - 4542.

9
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 ]