[ CAS No. 71989-20-3 ] {[proInfo.proName]}

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Quality Control of [ 71989-20-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 71989-20-3 ]

SDS Specification

Alternatived Products of [ 71989-20-3 ]

Product Details of [ 71989-20-3 ]

CAS No. :	71989-20-3	MDL No. :	MFCD00037137
Formula :	C₂₀H₂₀N₂O₅	Boiling Point :	-
Linear Structure Formula :	C₁₃H₉CH₂OCONHCH(CH₂)₂CONH₂CO₂H	InChI Key :	IZKGGDFLLNVXNZ-KRWDZBQOSA-N
M.W :	368.38	Pubchem ID :	2724775
Synonyms :	Fmoc-L-glutamine

Calculated chemistry of [ 71989-20-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.25
Num. rotatable bonds :	9
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	97.69
TPSA :	118.72 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.87
Log Po/w (XLOGP3) :	1.89
Log Po/w (WLOGP) :	2.24
Log Po/w (MLOGP) :	1.5
Log Po/w (SILICOS-IT) :	2.04
Consensus Log Po/w :	1.91

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.05
Solubility :	0.329 mg/ml ; 0.000892 mol/l
Class :	Soluble
Log S (Ali) :	-4.01
Solubility :	0.0364 mg/ml ; 0.0000987 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.87
Solubility :	0.00496 mg/ml ; 0.0000135 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.84

Safety of [ 71989-20-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 71989-20-3 ]

* 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 [ 71989-20-3 ]

[ 71989-20-3 ] Synthesis Path-Downstream 1~20

1
[ 122889-11-6 ]
[ 35737-15-6 ]
[ 35661-38-2 ]
[ 71989-20-3 ]
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}-3-carbamoyl-propylcarbamoyl)-2-(1H-imidazol-4-yl)-ethyl]-carbamic acid benzyl ester [ No CAS ]

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

2
[ 6214-20-6 ]
[ 108-24-7 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 77128-73-5 ]
Fmoc-Val [ No CAS ]
Ac-Val-NMeGln-Ser-NMePhe-NH₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 103 - 113

3
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 108-24-7 ]
[ 71989-20-3 ]
[ 198561-07-8 ]
Ac-Gln-Asp-Phe-Gly-OH [ No CAS ]

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

4
[ 71989-20-3 ]
Fmoc-Ala [ No CAS ]
[ 125238-99-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2004,vol. 77,p. 1915 - 1924

5
C₁₀H₁₅N₂O₅Pol [ No CAS ]
[ 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 ]
[ 71989-35-0 ]
[ 35661-38-2 ]
[ 71989-28-1 ]
[ 71989-16-7 ]
[ 71989-20-3 ]
[ 104091-08-9 ]
[ 143824-78-6 ]
C₄₂H₅₂N₇O₁₄Pol [ No CAS ]
C₄₄H₅₆N₇O₁₄Pol [ No CAS ]
C₄₅H₅₈N₇O₁₄Pol [ No CAS ]
C₄₅H₅₆N₇O₁₄Pol [ No CAS ]
C₄₆H₆₀N₇O₁₄Pol [ No CAS ]
C₄₅H₅₈N₇O₁₄PolS [ No CAS ]
C₄₆H₆₀N₇O₁₄Pol [ No CAS ]
C₄₈H₆₄N₇O₁₄Pol [ No CAS ]
C₄₇H₆₂N₇O₁₅Pol [ No CAS ]
C₄₇H₆₂N₇O₁₄PolS [ No CAS ]
C₄₇H₆₀N₇O₁₄Pol [ No CAS ]
C₄₈H₆₄N₇O₁₄Pol [ No CAS ]
C₄₉H₆₆N₇O₁₅Pol [ No CAS ]
C₄₈H₆₄N₇O₁₅Pol [ No CAS ]
C₄₉H₅₈N₇O₁₄Pol [ No CAS ]
C₅₁H₆₂N₇O₁₄Pol [ No CAS ]
C₅₀H₆₈N₇O₁₅Pol [ No CAS ]
C₄₅H₅₇N₈O₁₅Pol [ No CAS ]
C₄₇H₆₁N₈O₁₅Pol [ No CAS ]
C₄₉H₆₄N₇O₁₆Pol [ No CAS ]
C₅₃H₆₆N₇O₁₅Pol [ No CAS ]
C₅₁H₆₈N₇O₁₆Pol [ No CAS ]
C₅₁H₆₉N₈O₁₆Pol [ No CAS ]
C₅₃H₇₃N₈O₁₆Pol [ No CAS ]
C₅₆H₆₇N₈O₁₆Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 12h;Combinatorial reaction / High throughput screening (HTS);	Split & Mix Procedure for the Resin Bound HexapeptideP-Glu (OAll)-Gly-X1X2X3X4-H sublibrary The resin was suspended in 3:1 mixture of 1,2-dichloroethane (DCE) and DMF and equally partitioned into 17 4 mL Alltech tubes. Each tube thus contained 0.1/17 mmol=5.88 10-6 mol of resin-bound dipeptide. Excess solvent was removed in vacuo, and the resin was suspended in DMF (200 mL) and agitated for 30 minutes. The 17 amino acids (1.76 10-5 mmol, 3 eq for each step, 7.04 10-5 mmol for 4 steps) were weighed into 17 vials: 1. Fmoc-Ala-OH 22 mg 2. Fmoc-Asn-OH 25 mg 3. Fmoc-Asp(OtBu)-OH 29 mg 4. Fmoc-Gln-OH 26 mg 5. <strong>[104091-08-9]Fmoc-Glu(OtBu)-OH</strong> 30 mg 6. Fmoc-Gly-OH 21 mg 7. Fmoc-Ile-OH 25 mg 8. Fmoc-Leu-OH 25 mg 9. Fmoc-Lys(BOC)-OH 33 mg 10. Fmoc-Met-OH 26 mg 11. Fmoc-Phe-OH 27 mg 12. Fmoc-Pro-OH 24 mg 13. Fmoc-Ser(tBu)-OH 27 mg 14. Fmoc-Thr(tBu)-OH 28 mg 15. Fmoc-Trp(BOC)-OH 37 mg 16. Fmoc-Tyr(tBu)-OH 32 mg 17. Fmoc-Val-OH 24 mg Each amino acid was dissolved in DMF (2 mL); an aliquot of each solution (0.5 mL, corresponding to 1.76 10-5 mmol, 3 eq of each amino acid) was added to the appropriate tube. TBTU (1.76 10-5 mmol×17=2.99 10-4, 96 mg) and DIPEA (1.76 10-5 mmol×17=2.99 10-4, 52 mL) were separately dissolved in DMF (1.7 mL) and each solution was evenly distributed, delivering 3 eq of each reagent, to each one of the 17 tubes.The reaction tubes were agitated at room temperature for 12 hours, then the reagents and solvents were removed in vacuo and the resin was rinsed with DMF (2×1 mL each tube), DCM (2×1 mL each tube) and methanol (2×1 mL each tube). The resin was then suspended in 3:1 mixture of 1,2-dichloroethane and DMF and recombined. The recombined resin was acetylated (3 mL of acetylating reagent, 1 hour, room temperature) and deprotected (3 mL of 20% piperidine in DMF, 2 hours, room temperature).The procedure was repeated 3 more times. At the end of the 4th amino acid coupling the deprotection step was not executed.

Reference： [1]Patent: US6909006,2005,B1 .Location in patent: Page/Page column 30-31; 37

6
[ 159610-89-6 ]
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-32-4 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 446 - 457

7
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 1097192-04-5 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-30-2 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 446 - 457

8
Nα-Fmoc-Arg(NG-pbf)-Rink amide resin [ No CAS ]
[ 1097192-04-5 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 75932-02-4 ]
[ 198561-07-8 ]
[ 1217266-28-8 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 446 - 457

9
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 112883-29-1 ]
[ 35661-40-6 ]
[ 136083-57-3 ]
[ 104091-09-0 ]
[ 71989-23-6 ]
[ 35737-15-6 ]
[ 73731-37-0 ]
[ 71989-16-7 ]
[ 105047-45-8 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 91000-69-0 ]
[ 96402-49-2 ]
[ 94744-50-0 ]
Y-(α-aminoisobutyroyl)-EGTFTSDYSIYLDKKAQRAFVNWLLA-(α-aminoisobutyroyl)-KYG-(β-(1-naphthyl)-alaninoyl)-LDF-NH2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Solid phase peptide synthesis was performed on a CEM Liberty Peptide Synthesizer using standard Fmoc chemistry. TentaGel S Ram resin (1 g; 0.25 mmol/g) was swelled in NMP (10 ml) prior to use and transferred between tube and reaction vessel using DCM and NMP. Coupling (0148) An Fmoc-amino acid in NMP/DMF/DCM (1:1:1; 0.2 M; 5 ml) was added to the resin in a CEM Discover microwave unit together with HATU/DMF or COMU/DMF (0.5 M; 2 ml) and DIPEA/NMP (2.0 M; 1 ml). The coupling mixture was heated to 75° C. for 5 min while nitrogen was bubbled through the mixture. The resin was then washed with NMP (4×10 ml). Deprotection (0149) Piperidine/DMF (20percent; 10 ml) was added to the resin for initial deprotection and the mixture was heated by microwaves (30 sec; 40° C.). The reaction vessel was drained and a second portion of piperidine/NMP (20percent; 10 ml) was added and heated (75° C.; 3 min.) again. The resin was then washed with DMF (6×10 ml). Side Chain Acylation (0150) Fmoc-Lys(ivDde)-OH or alternatively another amino acid with an orthogonal side chain protective group was introduced at the position of the acylation. The N-terminal of the peptide backbone was then Boc-protected using Boc2O or alternatively by using a Boc-protected amino acid in the last coupling. While the peptide was still attached to the resin, the orthogonal side chain protective group was selectively cleaved using freshly prepared hydrazine hydrate (2-4percent) in NMP for 2×15 min. The unprotected lysine side chain was first coupled with Fmoc-Glu-OtBu or another spacer amino acid, which was deprotected with piperidine and acylated with a lipophilic moiety using the peptide coupling methodology as described above. Alternatively, the acylation moiety was introduced as a premade building block e.g. Fmoc-Lys(hexadecanoyl-gamma-Glu)-OH where gamm-Glu is the coupling of Glutamic acid through the side-chain. Abbreviations employed are as follows: COMU: 1-[(1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)-dimethylamino-morpholinomethylene)]methanaminium hexaflourophosphate ivDde: 1-(4,4-dimethyl-2,6-dioxocyclohexylidene)3-methyl-butyl Dde: 1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-ethyl DCM: dichloromethane DMF: N,N-dimethylformamide (0151) DIPEA: diisopropylethylamine EtOH: ethanol Et2O: diethyl ether HATU: N-[(dimethylamino)-1H-1,2,3-triazol[4,5-b]pyridine-1-ylmethylene]-N-methylmethanaminium hexafluorophosphate N-oxide MeCN: acetonitrile NMP: N-methylpyrrolidone (0152) TFA: trifluoroacetic acid TIS: triisopropylsilane Cleavage (0153) The resin was washed with EtOH (3×10 ml) and Et2O (3×10 ml) and dried to constant weight at room temperature (r.t.). The crude peptide was cleaved from the resin by treatment with TFA/TIS/water (95/2.5/2.5; 40 ml, 2 h; r.t.). Most of the TFA was removed at reduced pressure and the crude peptide was precipitated and washed three times with diethylether and dried to constant weight at room temperature. HPLC Purification of the Crude Peptide (0154) The crude peptide was purified to greater than 90percent by preparative reverse phase HPLC using a PerSeptive Biosystems VISION Workstation equipped with a C-18 column (5 cm; 10 mum) and a fraction collector and run at 35 ml/min with a gradient of buffer A (0.1percent TFA, aq.) and buffer B (0.1percent TFA, 90percent MeCN, aq.). Fractions were analyzed by analytical HPLC and MS and relevant fractions were pooled and lyophilized. The final product was characterized by HPLC and MS. (0155) The synthesized compounds are shown in Table 1 and Table 2

Reference： [1]Patent: US2015/299281,2015,A1 .Location in patent: Paragraph 0147-0155

10
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 112883-29-1 ]
[ 35661-40-6 ]
[ 136083-57-3 ]
[ 104091-09-0 ]
[ 71989-23-6 ]
[ 35737-15-6 ]
[ 73731-37-0 ]
[ 105047-45-8 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 77128-73-5 ]
[ 91000-69-0 ]
[ 116611-64-4 ]
C₁₅₀H₂₂₈N₄₀O₄₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: tGLP-1 and its analogues 2?13 were all synthesized using general solid-phase peptide synthesis of N-Fmoc/tBu chemistry. 63Fmoc Rink Amide-MBHA resin (0.1 mmol) was added to a 25 ml peptide synthetic vessel and swollen with DMF for 40 min. After deprotected by 25percent piperidine in DMF, a solution of Fmoc-AA-OH (0.4 mmol), HATU (0.4 mmol), HoAt (0.4 mmol) and DIPEA (0.8 mmol) in DMF was added to the vessel. After reacted for 1 h, the resin was washed three times with DMF and three times with CH2Cl2, then qualitative ninhydrin testing was performed to monitor whether some free amino groups still existed on the resin ornot. If not, the resin was washed three times with DMF again and repeated the procedures of deprotection and coupling. Forthe coupling of some unnatural amino acids, NMM instead of DIPEA and NMP instead of DMF were used. Besides, the reaction time was prolonged to 4 h. Following the final deprotection of N-terminus, the target peptide was cleaved from resin with Reagent K (TFA/thioanisole/water/phenol/EDT, 82.5:5:5:5:2.5) for 2 h atroom temperature. After filtration, the residue solution was concentrated, precipitated with cold diethyl ether and centrifuged for three times. The residue was dissolved in water and purified by Waters 2545 preparative RP-HPLC system. Sephadex G-25 was used for the further purification to remove some short peptide impurities. The molecular mass of the target peptide was confirmed by MALDI-TOF. The purity of peptide was tested with analytical RP-HPLC, and the conditions were as follows: a linear gradient of 20percent mobile phase A and 80percent mobile phase B to 80percent mobile phase A and 20percent mobile phase B (A: acetonitrile containing 0.1percent TFA; B: H2O containing 0.1percent TFA) in 30 min, at a flow rate of 1 mL/minute with UV detection at 214 nm.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1163 - 1170

11
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 112883-29-1 ]
[ 35661-40-6 ]
[ 136083-57-3 ]
[ 71989-23-6 ]
[ 35737-15-6 ]
[ 73731-37-0 ]
[ 105047-45-8 ]
[ 73724-45-5 ]
[ 71989-20-3 ]
[ 91000-69-0 ]
[ 116611-64-4 ]
[ 193954-26-6 ]
C₁₅₀H₂₂₈N₄₀O₄₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: tGLP-1 and its analogues 2-13 were all synthesized using general solid-phase peptide synthesis of N-Fmoc/tBu chemistry. 63Fmoc Rink Amide-MBHA resin (0.1 mmol) was added to a 25 ml peptide synthetic vessel and swollen with DMF for 40 min. After deprotected by 25% piperidine in DMF, a solution of Fmoc-AA-OH (0.4 mmol), HATU (0.4 mmol), HoAt (0.4 mmol) and DIPEA (0.8 mmol) in DMF was added to the vessel. After reacted for 1 h, the resin was washed three times with DMF and three times with CH2Cl2, then qualitative ninhydrin testing was performed to monitor whether some free amino groups still existed on the resin ornot. If not, the resin was washed three times with DMF again and repeated the procedures of deprotection and coupling. Forthe coupling of some unnatural amino acids, NMM instead of DIPEA and NMP instead of DMF were used. Besides, the reaction time was prolonged to 4 h. Following the final deprotection of N-terminus, the target peptide was cleaved from resin with Reagent K (TFA/thioanisole/water/phenol/EDT, 82.5:5:5:5:2.5) for 2 h atroom temperature. After filtration, the residue solution was concentrated, precipitated with cold diethyl ether and centrifuged for three times. The residue was dissolved in water and purified by Waters 2545 preparative RP-HPLC system. Sephadex G-25 was used for the further purification to remove some short peptide impurities. The molecular mass of the target peptide was confirmed by MALDI-TOF. The purity of peptide was tested with analytical RP-HPLC, and the conditions were as follows: a linear gradient of 20% mobile phase A and 80% mobile phase B to 80% mobile phase A and 20% mobile phase B (A: acetonitrile containing 0.1% TFA; B: H2O containing 0.1% TFA) in 30 min, at a flow rate of 1 mL/minute with UV detection at 214 nm.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1163 - 1170

12
[ 29022-11-5 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-28-1 ]
[ 132388-59-1 ]
[ 71989-20-3 ]
[ 55260-24-7 ]
[ 111061-56-4 ]
[ 143824-78-6 ]
C₅₆H₇₆N₁₆O₁₆S [ No CAS ]