Name: 135673-97-1 | Fmoc-Cha-OH
Brand: Ambeed
SKU: A751063
Rating: 4.6 (52 reviews)

1
[ 4100-13-4 ]
[ 35661-40-6 ]
[ 119831-72-0 ]
[ 135673-97-1 ]
[1,2,3]Thiadiazole-4-carboxylic acid {(S)-1-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-4-guanidino-butylcarbamoyl]-2-cyclohexyl-ethyl}-amide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 1423 - 1428.

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

References: [1]McComsey, David F.; Hawkins, Michael J.; Andrade-Gordon, Patricia; Addo, Michael F.; Oksenberg, Donna; Maryanoff, Bruce E. [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 10, p. 1423 - 1428].

3
[ 122889-11-6 ]
[ 35737-15-6 ]
[ 35661-38-2 ]
[ 135673-97-1 ]
Cbz-His-OH [ No CAS ]
[(R)-1-((R)-1-{(R)-2-Benzyloxy-1-[(R)-1-((S)-1-carbamoyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-ethylcarbamoyl}-2-cyclohexyl-ethylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester [ No CAS ]

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

4
[ 35661-60-0 ]
[ 71989-18-9 ]
[ 104091-08-9 ]
[ 135673-97-1 ]
H-Cys(Trt)-2-chlorotrityl resinFmoc-Asp(OtBu)-OH [ No CAS ]
(S)-4-{(S)-2-[(R)-2-((S)-2-Amino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-4-methyl-pentanoylamino}-4-[(S)-1-((R)-1-carboxy-2-mercapto-ethylcarbamoyl)-2-cyclohexyl-ethylcarbamoyl]-butyric acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 203 - 206.

5
[ 35661-60-0 ]
[ 71989-18-9 ]
[ 108-24-7 ]
[ 104091-08-9 ]
[ 135673-97-1 ]
H-Cys(Trt)-2-chlorotrityl resinFmoc-Asp(OtBu)-OH [ No CAS ]
(S)-4-{(S)-2-[(R)-2-((S)-2-Acetylamino-3-carboxy-propionylamino)-4-carboxy-butyrylamino]-4-methyl-pentanoylamino}-4-[(S)-1-((R)-1-carboxy-2-mercapto-ethylcarbamoyl)-2-cyclohexyl-ethylcarbamoyl]-butyric acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 203 - 206.

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2955 - 2963.

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 3630 - 3638.

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

9
[ 132684-59-4 ]
[ 125238-99-5 ]
[ 135673-97-1 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1186310-46-2 ]

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

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6822 - 6856.

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 6822 - 6856.

Yield	Reaction Conditions	Operation in experiment
95%		The molecular scaffold 3 was synthesized using standard solid-phase peptide synthesis methods. The 2-chlorotrityl-chloride resin (Novabiochem, loading 1.4 mmol/g) was used as solid support. For loading of the resin (100 mg, 0.14 mmol) 2 equiv. Fmoc-protected amino acid and 3 equiv. DIPEA (74 mul, 0.42 mmol) were dissolved in 2 ml CH2Cl2 and the reaction mixture was added to the resin. The reaction mixture was shaken overnight at room temperature. The resin was washed three times with 2 ml CH2Cl2 and 2 ml DMF. For Fmoc-deprotection the resin was treated two times for 15 min. with 2 ml 30 percent piperidine/DMF. A standard protocol was used for solid phase peptide synthesis: 4 equiv. Fmoc-protected amino acid, 4 equiv. HBTU (212 mg, 0.56 mmol), 4 equiv. HOBt (76 mg, 0.56 mmol) and 8 equiv. DIPEA (196 ml, 1.12 mmol) were dissolved in 2 ml CH2Cl2/DMF (1/1; v/v). The reaction mixture was stirred 20 min. at room temperature and then added to the resin. The reaction mixture was shaken for 2 hours at room temperature.For the cleavage of the peptide 3 from the solid-phase the resin was treated two times for 15 min. with 2 ml 2 percent TFA/CH2Cl2 (v/v). The solvent was co-evaporated with toluene under reduced pressure and the product was purified by preparative HPLC (H2O + 0.1 percent TFA; 10-95 percent CH3CN, 15 min, 120 ml/min, column: Sun Fire 50x100 mm, Waters).

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 1055 - 1061.

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 8-(9-fluorenylmethyloxycarbonyl-amino)-3,6-dioxaoctanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 16h; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; C₃₈H₄₁N₃O₈; Fmoc-Lys(tert-butoxycarbonyl); N-(9-fluorenylmethoxycarbonyl)-D-alanine; (S)-3-cyclohexyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid Further stages;

References: [1]Wilkinson, Brendan L.; Day, Stephanie; Chapman, Robert; Perrier, Sébastien; Apostolopoulos, Vasso; Payne, Richard J. [Chemistry - A European Journal, 2012, vol. 18, # 51, p. 16540 - 16548].