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

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Quality Control of Fmoc-D-Glu(OtBu)-OH Purity: 97% SDS Specification

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Product Citations

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-D-Glu(OtBu)-OH

CAS No. :	104091-08-9
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
MDL No. :	MFCD00077055
InChI Key :	OTKXCALUHMPIGM-HXUWFJFHSA-N
Pubchem ID :	7018822

Safety of Fmoc-D-Glu(OtBu)-OH

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

Application In Synthesis of Fmoc-D-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 [ 104091-08-9 ]

[ 104091-08-9 ] Synthesis Path-Downstream 1~36

1
C₁₄H₂₄N₃O₇Pol [ No CAS ]
[ 104091-08-9 ]
C₃₈H₄₉N₄O₁₂Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 1h;	Commercially available Nalpha-(9-Fluorenylmethoxycarbonyl)-D-glutamic acid 7-t-butyl ester (1.14 g), TBTU (0.87 g), HOBt (0.37 g) and DIPEA (940 muL) as a solution in NMP (20 mL) was added to compound 5. The reaction mixture was shaken for one hour. The reaction mixture was filtered through a glass sinter funnel then the solid was washed with N-methylpyrrolidine (3×15 mL), methanol (3×15 mL), and again with N-methylpyrrolidine (3×15 mL). The reaction was judged to be complete using the Kaiser Test (vide supra), yielding the resin bound compound 79.

References: [1]Patent: US2008/51326,2008,A1 .Location in patent: Page/Page column 333.

2
C₁₈H₃₁N₄O₈Pol [ No CAS ]
[ 104091-08-9 ]
C₄₂H₅₆N₅O₁₃Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 17h;	Commercially available Nalpha-(9-Fluorenylmethoxycarbonyl)-D-glutamic acid gamma-t-butyl ester (0.98 g), TBTU (0.74 g), HOBt (0.31 g) and DIPEA (810 muL) as a solution in NMP (20 mL) was added to compound 71 (1.8 g). The reaction mixture was shaken for seventeen hours. The reaction mixture was filtered through a glass sinter funnel then the solid was washed with N-methylpyrrolidine (3×15 mL), methanol (3×15 mL), and again with N-methylpyrrolidine (3×15 mL) to give compound 85.

References: [1]Patent: US2008/51326,2008,A1 .Location in patent: Page/Page column 334.

3
C₂₅H₄₄N₅O₁₀Pol [ No CAS ]
[ 104091-08-9 ]
C₄₉H₆₉N₆O₁₅Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; for 3h;	Commercially available Nalpha-(9-Fluorenylmethoxycarbonyl)-D-glutamic acid gamma-t-butyl ester (2.29 g), TBTU (1.73 g), HOBt (0.73 g) and DIPEA (1.9 mL) as a solution in NMP (25 mL) were added to compound 114 (3.3 g). The mixture was shaken for three hours. The reaction mixture was filtered through a glass sinter funnel then the solid was washed with N-methylpyrrolidine (3×25 mL), methanol (3×25 mL), and again with N-methylpyrrolidine (3×25 mL) to give compound 120.

References: [1]Patent: US2008/51326,2008,A1 .Location in patent: Page/Page column 338.

4
[ 59524-02-6 ]
[ 104091-08-9 ]
Boc-Ser(Fmoc-D-Glu(OtBu))-OBzl [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1720 - 1730.

5
[ 140422-54-4 ]
[ 104091-08-9 ]
Boc-Thr(Fmoc-D-Glu(OtBu))-OBzl [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 1720 - 1730.

6
[ 84793-07-7 ]
[ 104091-08-9 ]
[ 1562-93-2 ]
N-[4-phenylazobenzoyl]-D-α-glutamyl-glutamic acid [ No CAS ]