Fmoc-Asp(OtBu)-OH | Carboxylic Acids

Structure of Fmoc-Asp(OtBu)-OH
CAS No.: 71989-14-5

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Synonyms: 4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate; Fmoc-L-Asp(OtBu)-OH

4.5 *For Research Use Only !

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Quality Control of [ 71989-14-5 ] Purity: 98% SDS Specification

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Product Citations Show More

Cell-active peptide inhibitors of the FANCM-RMI interaction

Alcock, Lisa J ; Mills, Joshua ; Bythell-Douglas, Rohan ; Sudhakar, Haritha Krishna ; Deshpande, Chandrika ; Passioura, Toby , et al.

DOI: 10.26434/chemrxiv-2025-fn5l3 ChemRxiv,2025.

Abstract: The FANCM-RMI protein-protein interaction plays an essential role in cancers that extend their telomeres through the Alternative Lengthening of Telomeres (ALT) pathway. Here, we report the first cell-active peptide inhibitors of FANCM-RMI. Screening of mRNA-displayed peptide libraries treated with trans-1,4-dibromo-2-butene led to the discovery of both linear and cyclic peptide hits that bind RMI at the FANCM interaction site. The most potent peptides engage RMI with nanomolar affinity (KD = 4-37 nM) and outcompete the native peptide mimic of FANCM (IC₅₀ = 24-155 nM). A bound X-ray crystal structure of the optimal peptide hit revealed novel interactions at the RMI binding site that are not found in the native interaction. Conjugation to a cell-penetrating peptide resulted in inhibitors that induced an antiproliferative effect in ALT-positive osteosarcoma cell lines. These inhibitors represent the first bioactive RMI binders that can be used as chemical tools for studying the involvement of FANCM-RMI in ALT-driven cancers.

Purchased from AmBeed: 71989-14-5 ; 71989-33-8 ; 71989-35-0

Comparison of Technetium-99m-Labeled Pentapeptides as Bone Imaging Agents: Influence of Different Types of Acidic Amino Acids

Effendi, Nurmaya ; Munekane, Masayuki ; Malik, Abd ; Putra, Amal Rezka ; Patrianesha, Bisma Barron ; Ritawidya, Rien , et al.

DOI: 10.1248/cpb.c25-00530 PubMed ID: 41161797 Chem. Pharm. Bull.,2025,73(10):1010-1016.

Abstract: Bone-seeking radiopharmaceuticals are essential for the early detection of bone metastases. In this study, we developed three Technetium-99m (^99mTc)-labeled oligopeptides composed of acidic amino acids and evaluated their bone-targeting ability. Hydrazinonicotinamide (HYNIC)-conjugated oligopeptides with five residues of aspartic acid (Asp), glutamic acid (Glu), or γ-carboxyglutamic acid (Gla) were synthesized and radiolabeled with ^99mTc using tricine and 3-acetylpyridine as co-ligands. Their hydroxyapatite binding, in vitro stability, biodistribution, and single-photon emission computed tomography (SPECT)/CT imaging in normal mice were evaluated. Among the three tracers, [^99mTc]Tc-HYNIC-(tricine)(AcP)-(dl-Gla)₅ ([^99mTc]3) showed the highest hydroxyapatite binding and bone uptake, with clear visualization in SPECT/CT. All compounds exhibited high radiochemical purity and in vivo stability. Oligopeptides containing Gla residues exhibited superior bone affinity and imaging performance, suggesting that Gla-based oligopeptides are promising scaffolds for the development of ^99mTc-labeled bone imaging agents.

Keywords: bone-seeking agent ; bone metastasis ; Tc-99m ; peptide ; nuclear medicine imaging

Purchased from AmBeed: 71989-14-5 ; 204251-24-1 ; 934816-82-7

Product Details of [ 71989-14-5 ]

CAS No. :	71989-14-5
Formula :	C₂₃H₂₅NO₆
M.W :	411.45
SMILES Code :	O=C(OC(C)(C)C)C[C@@H](C(O)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O
Synonyms :	4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate; Fmoc-L-Asp(OtBu)-OH
MDL No. :	MFCD00037131
InChI Key :	FODJWPHPWBKDON-IBGZPJMESA-N
Pubchem ID :	2724635

Safety of [ 71989-14-5 ]

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

Computational Chemistry of [ 71989-14-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	30
Num. arom. heavy atoms	12
Fraction Csp3	0.35
Num. rotatable bonds	10
Num. H-bond acceptors	6.0
Num. H-bond donors	2.0
Molar Refractivity	110.53
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.	2.84
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	3.5
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.71
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.	2.56
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	3.32
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.19

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.23
Solubility	0.0241 mg/ml ; 0.0000586 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.	-5.32
Solubility	0.00195 mg/ml ; 0.00000475 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	-5.74
Solubility	0.000749 mg/ml ; 0.00000182 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	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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.32 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	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<2.0
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)	4.07

Application In Synthesis of [ 71989-14-5 ]

* 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.

Upstream synthesis route of [ 71989-14-5 ]
Downstream synthetic route of [ 71989-14-5 ]

[ 71989-14-5 ] Synthesis Path-Upstream 1~1

1
[ 71989-14-5 ]
[ 209252-17-5 ]

References: [1] Synthesis, 1998, # 6, p. 837 - 841.
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662.
[3] Patent: US2014/39153, 2014, A1, .

[ 71989-14-5 ] Synthesis Path-Downstream 1~55

1
[ 20866-48-2 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 125238-99-5 ]
[ 110116-75-1 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2094 - 2099.

2
[ 20866-48-2 ]
[ 71989-14-5 ]
[ 77128-73-5 ]
(R)-N₅-(tert.-butoxy-carbonyl)-N₂-(9-fluorenylmethoxycarbonyl)-ornithine [ No CAS ]
[ 106327-80-4 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2094 - 2099.

3
[ 122889-11-6 ]
[ 71989-14-5 ]
[ 35737-15-6 ]
[ 35661-38-2 ]
Cbz-His-OH [ No CAS ]
(R)-N-{(R)-2-Benzyloxy-1-[(R)-1-((S)-1-carbamoyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-ethyl}-3-[(R)-2-benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-succinamic acid [ No CAS ]

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

4
[ 67-56-1 ]
[ 122889-11-6 ]
[ 71989-14-5 ]
[ 708-06-5 ]
Gly-Wang resin [ No CAS ]
(S)-N-[(S)-2-Benzyloxy-1-(methoxycarbonylmethyl-carbamoyl)-ethyl]-3-[1-(2-hydroxy-naphthalen-1-yl)-meth-(E)-ylidene]-amino}-succinamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 10676 - 10681.

5
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 108-24-7 ]
[ 198561-07-8 ]
Ac-Asp-Asp-Phe-Gly-OH [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 2469 - 2472.

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
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 86123-10-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
[ 1424402-71-0 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1853 - 1864.

9
[ 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.

10
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 103213-32-7 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
Fmoc-[β-dimethylcysteine](Trt)-OH [ No CAS ]
C₅₅H₇₀N₁₀O₁₁S₂ [ No CAS ]

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

11
[ 35661-60-0 ]
[ 122889-11-6 ]
[ 71989-14-5 ]
[ 64-19-7 ]
[ 378247-75-7 ]
Fmoc-Glu(pg)-OH [ No CAS ]
C₃₈H₄₆N₆O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Synthesis of NH2-ACC-Rink Amide resin. Preparation of ACC wascarried out as described previously according to Maly et al.18 To glass reactionvessel, 1 eq (6.24 mmol, 13 g) of Rink AM resin was added and stirred gentlyonce per 10 min in DCM for 1 h, and then filtered and washed 3 times with DMF.Fmoc-protecting group was removed using 20percent piperidine in DMF (5, 5, and25 min), filtered each time and washed with DMF (six times). Next, 2.50 eq of Fmoc-ACC-OH (15.6 mmol, 6.9 g) was preactivated with 2.50 eq HOBt monohydrate (15.6 mmol, 2.34 g) and 2.50 eq DICI (15.6 mmol, 2.0 ml) in DMFand mixture was added to the resin. Reaction was stirred gently for 24 h at room temperature. Resin was washed four times with DMF and reaction was repeatedusing 1.5 eq of above reagents to improve yield of ACC coupling to the resin. Afterreaction, resin was washed with DMF and Fmoc group was removed using 20percentpiperidine in DMF (5, 5, and 25 min), filtered and washed with DMF (six times). Synthesis of NH2-Asp(t-Bu)-ACC-Rink Amide resin. Next, 2.5 eqFmoc-Asp(t-Bu)-OH (15.6 mmol, 6.42 g) with 2.5 eq HATU (15.6 mmol, 5.93 g),2.5 eq collidine (15.6 mmol, 2.03 ml) in DMF were activated for 2 min and added tofilter cannula with 1 eq (6.24 mmol) NH2-ACC-resin and reaction was carried outfor 24 h. Next, resin was washed four times with DMF and reaction was repeatedusing 1.5 eq of above reagents. After washing with DMF, Fmoc-protecting groupwas removed using 20percent piperidine in DMF (5, 5, and 25 min). Resin wasadditional washed with DCM (3 times) and MeOH (3 times) and dried over P2O5. Synthesis of individual optimized substrates. The 2.5 eqFmoc-P2-OH was preactivated with 2.5 eq HOBt and 2.5 eq DICI in DMF andadded to cartridge with 1 eq NH2-Asp(t-Bu)-ACC-resin (all substrates containedAsp at P1 position) and followed by gentle agitation for 3 h. Then, it was filteredand washed with DMF (six times). Fmoc-protecting group was removed using 20percent piperidine in DMF (5, 5, and 25 min). Ninhydrin test was carried out each time aftercoupling and deprotection. A solution of 2.5 eq Fmoc-P3-OH, 2.5 eq HOBt, and2.5 eq DICI in DMF was added to the resin and the slurry was agitated for 3 h.After removal of the solution, the resin was washed with DMF (six times), andcoupling and deprotection of Fmoc-P4-OH was carried in identical conditions likeP2 position. N-terminus was protected with acetyl group using 5 eq AcOH, 5 eqHBTU, and 5 eq DIPEA in DMF as previous described. After solvent removal, theresin was washed with DMF (six times), DCM (three times), and MeOH (threetimes) dried over P2O5 and cleaved from the resin with a mixture of TFA/TIPS/H2O(percent, v/v/v 95 : 2.5 : 2.5). The crude product was purified by HPLC and lyophilized.Its purity was confirmed by analytical HPLC. Each optimized substrate wasanalyzed using HRMS. Optimized substrates were dissolved in peptide gradeDMSO to 20mM concentration and stored at -80 °Cuntil use.

References: [1]Cell Death and Differentiation,2014,vol. 21,p. 1482 - 1492.

12
[ 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.

13
[ 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.

14
[ 1026023-54-0 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 556-08-1 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 109425-51-6 ]
[ 116821-47-7 ]
[ 198561-07-8 ]
[ 334918-39-7 ]
C₁₂₈H₂₁₈N₅₀O₃₆ [ No CAS ]