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L-Tryptophan,α-methyl-
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Name

L-Tryptophan,α-methyl-

 EINECS N/A
CAS No. 16709-25-4 Density 1.314 g/cm3
PSA 79.11000 LogP 2.13100
Solubility N/A Melting Point 168-172 °C
Formula C12H14N2O2 Boiling Point 444 °C at 760 mmHg
Molecular Weight 218.255 Flash Point 222.3 °C
Transport Information N/A Appearance Colourless solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 16709-25-4 (ALPHA-METHYL-L-TRYPTOPHAN) Hazard Symbols N/A
Synonyms

Tryptophan,α-methyl-, L- (8CI);(-)-α-Methyltryptophan;L-α-Methyltryptophan;α-Methyl-(S)-tryptophan;α-Methyl-L-tryptophan;

Article Data 10

L-Tryptophan,α-methyl- Synthetic route

114524-80-0

methyl 2-(indol-3-ylmethyl)-2-aminopropionate

A

56452-52-9

α-methyl-DL-tryptophan

B

16709-25-4

(S)-α-methyltryptophan

C

96551-27-8

α-methyl-(R)-tryptophan methyl ester

Conditions
ConditionsYield
With α-chymotrypsin In water at 37℃; for 40h; pH=5.0;A 4%
B n/a
C 88%
With α-chymotrypsin In water at 37℃; for 40h; pH=5.0;A 4%
B n/a
C n/a
114524-80-0

methyl 2-(indol-3-ylmethyl)-2-aminopropionate

A

16709-25-4

(S)-α-methyltryptophan

B

96551-27-8

α-methyl-(R)-tryptophan methyl ester

Conditions
ConditionsYield
With α-chymotrypsin In water at 37℃; for 40h; Product distribution; also other α-methyl-amino acid esters investigated;A n/a
B 88%
116139-87-8

(S)-N2-benzoyl-2-methyltryptophan-methylester

16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;87%
1266681-04-2

tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate

16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
Stage #1: tert-butyl 3-{[(3S,5aR,6aS,7aS)-2,3,5,5a,6,6a,7,7a-octahydro-3,6,6,7a-tetramethyl-2-oxobicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-3-yl]methyl}-1H-indole-1-carboxylate With cesium hydroxide; water In ethanol at 70℃; for 4h;
Stage #2: With hydrogenchloride In water		86%

tert-butyl [3-(3S,6R)-N-1-(tert-butoxycarbonyl)-6-isopropyl-3-methyl-2-oxo-5-phenyl-1,2,3,6-tetrahydropyrazinylmethyl]-1H-1-indolecarboxylate

16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogenchloride at 150℃; for 72h; Hydrolysis;40%
141784-94-3

2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

A

16709-25-4

(S)-α-methyltryptophan

B

141784-97-6

(R)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

C

141784-94-3, 141784-97-6

(S)-2-Amino-3-(1H-indol-3-yl)-2-methyl-propionic acid butyl ester

Conditions
ConditionsYield
In various solvent(s) Ambient temperature; Candida lipolythica lipase (active component: Candida lypolythica esterase); Yield given. Yields of byproduct given;
In various solvent(s) Ambient temperature; Candida lipolythica lipase (active component: Candida lypolythica esterase); Yield given. Yields of byproduct given. Title compound not separated from byproducts;
121704-33-4

2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid

A

16709-25-4

(S)-α-methyltryptophan

B

121704-33-4

(R)-2-(2-Chloro-acetylamino)-3-(1H-indol-3-yl)-2-methyl-propionic acid

Conditions
ConditionsYield
With potassium hydroxide; potassium phosphate buffer; porcine kidney acylase I at 40℃; relative initial rate of hydrolysis, also with Aspergillus acylase I as a catalyst; with or without CoCl2;

(R)-Nα-(Methoxycarbonyl)-α-methyltryptophan methyl ester

A

56452-52-9

α-methyl-DL-tryptophan

B

16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogenchloride for 16h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-propyl)-indole-1-carboxylic acid benzyl ester

16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol for 3h; Ambient temperature; Yield given;
153-91-3

DL-α-methyltryptophan

A

56452-52-9

α-methyl-DL-tryptophan

B

16709-25-4

(S)-α-methyltryptophan

Conditions
ConditionsYield
resolution of racemate via chiral HPLC;
With Merck RP-18 WF254S plates coated with Nτ-n-decyl-L-spinacine and Cu acetate In water; acetonitrile Resolution of racemate;

L-Tryptophan,α-methyl- Specification

The CAS register number of L-Tryptophan,α-methyl- is 16709-25-4. It also can be called as L-α-Methyltryptophan and the systematic name about this chemical is α-methyl-L-tryptophan. The molecular formula about this chemical is C12H14N2O2 and the molecular weight is 218.25. It belongs to the following product categories which include Amino Acids 13C, 2H, 15N; Amino Acids & Derivatives; Chiral Reagents; Heterocycles; Indole Derivatives and so on. The usage of this chemical is a therapeutic and carrier molecule.

Physical properties about L-Tryptophan,α-methyl- are: (1)ACD/LogP: 1.39; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 4; (9)Polar Surface Area: 34.47 Å2; (10)Index of Refraction: 1.675; (11)Molar Refractivity: 62.4 cm3; (12)Molar Volume: 166 cm3; (13)Polarizability: 24.74x10-24cm3; (14)Surface Tension: 65.7 dyne/cm; (15)Density: 1.314 g/cm3; (16)Flash Point: 222.3 °C; (17)Enthalpy of Vaporization: 73.96 kJ/mol; (18)Boiling Point: 444 °C at 760 mmHg; (19)Vapour Pressure: 1.15E-08 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@](N)(C)Cc2c1ccccc1nc2
(2)InChI: InChI=1/C12H14N2O2/c1-12(13,11(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,14H,6,13H2,1H3,(H,15,16)/t12-/m0/s1
(3)InChIKey: ZTTWHZHBPDYSQB-LBPRGKRZBW
(4)Std. InChI: InChI=1S/C12H14N2O2/c1-12(13,11(15)16)6-8-7-14-10-5-3-2-4-9(8)10/h2-5,7,14H,6,13H2,1H3,(H,15,16)/t12-/m0/s1
(5)Std. InChIKey: ZTTWHZHBPDYSQB-LBPRGKRZSA-N

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