Name: Fmoc-Glu(OtBu)-OH | (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid
Brand: Ambeed
SKU: A165615

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Fmoc-Glu(OtBu)-OH is a protected glutamic acid derivative with the amino group protected by 9-fluorenylmethoxycarbonyl (Fmoc) and the carboxyl group esterified by tert-butyl, suitable for peptide synthesis.

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

4.5 *For Research Use Only !

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Quality Control of Fmoc-Glu(OtBu)-OH Purity: 98% contains ~4% water SDS Specification

COA

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NMR

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CNMR

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HPLC

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LC-MS

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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.

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 Fmoc-Glu(OtBu)-OH

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 Fmoc-Glu(OtBu)-OH

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

Application In Synthesis of Fmoc-Glu(OtBu)-OH

* 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 1~35

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 ]