D(+)-Tryptophan supplier | CasNO.153-94-6

Name
D(+)-Tryptophan
EINECS 205-819-9
CAS No. 153-94-6
Article Data79
CAS DataBase
Density 1.362 g/cm³
Solubility 11 g/L (20 °C) in water
Melting Point 282-285 °C
Formula C₁₁H₁₂N₂O₂
Boiling Point 447.9 °C at 760 mmHg
Molecular Weight 204.228
Flash Point 224.7 °C
Transport Information
Appearance White or yellow crystalline powder
Safety 24/25-36/37/39-36-26
Risk Codes 36/37/38-41-37/38-22
Molecular Structure
Hazard Symbols Xi
Synonyms (R)-tryptophan;(+)-Tryptophan;(2R)-2-azaniumyl-3-(1H-indol-3-yl)propanoate;Tryptophan, D-;(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid;H-D-Trp-OH;
PSA 79.11000
LogP 1.82260

Synthetic route

: C15H15N3*C18H14Cl2N2O3

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With benzylamine hydrochloride In water; isopropyl alcohol at 20℃; for 1h;	95%

: 392-12-1
Indole-3-pyruvic acid

A: 73-22-3
L-Tryptophan

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With CC10H14NOSCH2CH2CH3N(CH3)2 (5); zinc diacetate In methanol at 30℃; Product distribution; pH 4.00;	A 6% B 94%
With 5-((3-(dimethylamino)propyl)thio)-4-(aminomethyl)-3-hydroxyl-5,6,7,8-tetraquinoline In methanol at 30℃; Product distribution; stereoselective transaminations at pH=4.00, various reagents;	A 6 % Chromat. B 94 % Chromat.
With phosphate buffer; 6A-monoimidazolyl-6B-(5'-thiopyridoxaminyl)-β-D-cyclodextrin In water at 25℃; Product distribution; other reragents, various pH;

: 120-72-9
indole

: 56-45-1
L-serin

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
Stage #1: indole; L-serin With Salmonella enterica tryptophan synthase In methanol; aq. phosphate buffer at 37℃; pH=8.0; Enzymatic reaction; Stage #2: With (2R)-aspartic acid In methanol; aq. phosphate buffer pH=8.0; Stage #3: In aq. phosphate buffer; deuteromethanol at 37℃; pH=8.0; Enzymatic reaction; stereoselective reaction;	69%

: 66872-76-2
β-(3-indolyl)-α-ketopropanoic acid sodium salt

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With zinc(II) perchlorate; (S)-15-amino-methyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridinophane In methanol for 24h; Ambient temperature;	62%

: 54-12-6
Trp

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With sodium hydroxide; oxygen; 2-amino-2-hydroxymethyl-1,3-propanediol In water at 30℃; for 8h; pH=7.3; Resolution of racemate; Enzymatic reaction; enantioselective reaction;	48%

: 54-12-6
Trp

A: 73-22-3
L-Tryptophan

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With Bis(2-ethylhexyl)phosphoric acid; sodium dodecyl-sulfate; O,O'-dibenzoyl-L-tartaric acid In octanol; water at 20℃; for 4h; Reflux; Resolution of racemate; optical yield given as %ee; enantioselective reaction;	A n/a B 18.59%
With (2R,3R,11R,12R)-(+)-18-crown-6-2,3,11,12-tetracarbonic acid In acetonitrile at 25℃; pH=3; Electrochemical reaction;
With teicoplanin In methanol; water Product distribution; Further Variations:; Reagents; pH-values; Solvents;

: 4299-70-1, 7303-49-3, 22032-65-1
D-Tryptophan methyl ester

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With barium dihydroxide; water
With methanol; barium dihydroxide
With Streptomyces spp. 82F2 D-aminopeptidase In dimethyl sulfoxide at 20℃; for 0.0833333h; pH=6.5; aq. buffer; Enzymatic reaction;

: 2280-01-5
N-acetyl-D-tryptophan

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With hydrogenchloride; water
With sulfuric acid; water
With barium dihydroxide; water
With D-aminoacylase; cobalt(II) chloride hexahydrate at 36 - 37℃; pH=7.4; aq. phosphate buffer; Enzymatic reaction;

: 742100-62-5
Nα-chloroacetyl-D-tryptophan

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With sulfuric acid; water

: 2279-15-4
N-(benzyloxycarbonyl)-D-tryptophan

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With methanol; palladium; acetic acid Hydrogenation;

: 120-72-9
indole

: 56-45-1
L-serin

A: 127-17-3
2-oxo-propionic acid

B: 73-22-3
L-Tryptophan

C: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
N+C5Ala2C16; PL+C2N2C16; copper(II) perchlorate In water at 30℃; for 200h; Product distribution; aq. acetate buffer (pH 5.0, KCl), other catalysts, also with D-serine and DL-serine;

...Expand

: 5457-31-8
(3-indolylmethyl)trimethylammonium iodide

: 56-40-6
glycine

A: 73-22-3
L-Tryptophan

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
Yield given. Multistep reaction;
With hydrogenchloride; sodium hydroxide; S-2-N-(N'-benzylprolyl)aminibenzophenone; sodium methylate 1.) methanol, 2.) acetonitrile, 20 deg C, 3 h, 3.) methanol, reflux; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: DL-5-indolylmethylhydantoin

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 8.0; enzymatic reaction;

: 54896-75-2
N-carbamyl-D-tryptophan

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h;
With potassium phosphate buffer; Pseudomonas sp. AJ-11220 In various solvent(s) at 30℃; for 2h; pH 7.5; enzymatic reaction;

: 82704-14-1
(S)-2-{(N-benzyl-2-pyrrolidinyl)carbonylamino}benzaldehyde

: 54-12-6
Trp

A: 73-22-3
L-Tryptophan

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With hydrogenchloride; sodium methylate; nickel(II) nitrate Product distribution; 1.) MeOH, 40 deg C, 24 h, 2.) reflux;

...Expand

: H-Arg-D-Trp-NmePhe-D-Trp-Leu-Met-NH2

A: 74-79-3
L-arginine

B: 2566-30-5
N-Methyl-L-phenylalanine

C: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With base In water Product distribution; other reagent;

...Expand

D-tryptophan-ethyl ester: D-tryptophan-ethyl ester

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With sodium hydroxide; ethanol; water

D-tryptophan-isopropyl ester: D-tryptophan-isopropyl ester

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With hydrogenchloride; water

6A-(2-(2-(2-aminoethylamino)ethylamino)ethylamino)-6A-deoxy-β-cyclodextrin (R)-tryptophan complex: 6A-(2-(2-(2-aminoethylamino)ethylamino)ethylamino)-6A-deoxy-β-cyclodextrin (R)-tryptophan complex

A: 153-94-6
D-tryptophan

B 6A-(2-(2-(2-aminoethylamino)ethylamino)ethylamino)-6A-deoxy-β-cyclodextrin: 6A-(2-(2-(2-aminoethylamino)ethylamino)ethylamino)-6A-deoxy-β-cyclodextrin

Conditions

Conditions	Yield
With sodium perchlorate In water at 25.05℃; Equilibrium constant; Further Variations:; pH-values; decomplexation;

6A-deoxy-6A-(1,4,7,10-tetraazacyclododecan-1-yl)-β-cyclodextrin (R)-tryptophan complex: 6A-deoxy-6A-(1,4,7,10-tetraazacyclododecan-1-yl)-β-cyclodextrin (R)-tryptophan complex

A: 153-94-6
D-tryptophan

B 6A-deoxy-6A-(1,4,7,10-tetraazacyclododecan-1-yl)-β-cyclodextrin: 6A-deoxy-6A-(1,4,7,10-tetraazacyclododecan-1-yl)-β-cyclodextrin

Conditions

Conditions	Yield
With sodium perchlorate In water at 25.05℃; Equilibrium constant; Further Variations:; pH-values; decomplexation;

: 4299-70-1, 7303-49-3, 22032-65-1
D-Tryptophan methyl ester

A: 67-56-1
methanol

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics;

: 7303-49-3
DL-tryptophan methyl ester

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: di-O-benzoyl-Lg-tartaric acid 2: Ba(OH)2; water View Scheme
Multi-step reaction with 2 steps 1: beim Behandeln mit Pankreas-Enzym in wss. Loesung 2: Ba(OH)2; methanol View Scheme

: 1218-34-4, 87-32-1
N-acetyl-DL-tryptophan

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: beim Behandeln mit Hilfe von Amidase aus Aspergillus oryzae oder Penicillium vinaceum 2: H2SO4; water View Scheme
Multi-step reaction with 2 steps 1: quinine 2: H2SO4; water View Scheme
Multi-step reaction with 2 steps 1: brucine 2: HCl; water View Scheme

: 79189-76-7
N2-(chloroacetyl)-DL-tryptophan

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pancreas-enzyme / arbeiten in wss. Loesung bei pH 7.6 2: H2SO4; water View Scheme

(PPh3)2 PdCl2: (PPh3)2 PdCl2

: 1-acetamido-2-(3-indolyl)ethene

: 2-(2-isopropyl-5-methylcyclohexyloxy)ethanol

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With CO In tetrahydrofuran; hydrogenchloride

...Expand

: 1-acetamido-2-(3-indolyl)ethene

: 2-(2-isopropyl-5-methylcyclohexyloxy)ethanol

: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With CO; (PPh3)2PdCl2 In tetrahydrofuran; hydrogenchloride

: 107911-05-7
trans-cyclo-(D-tryptophanyl-L-tyrosyl)

A: 60-18-4
L-tyrosine

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With hydrogenchloride; water at 110℃; for 16h;

: 338-69-2
D-Alanine

: 392-12-1
Indole-3-pyruvic acid

A: 127-17-3
2-oxo-propionic acid

B: 153-94-6
D-tryptophan

Conditions

Conditions	Yield
With pyridoxal 5'-phosphate; recombinant Lactobacillus salivarius UCC118 D-amino acid aminotransferase In aq. phosphate buffer at 30℃; for 0.0166667h; pH=7.5; Enzymatic reaction;

...Expand

: 67-56-1
methanol

: 153-94-6
D-tryptophan

: 14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8
(R)-(+)-tryptophan methyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 4h; Heating;	100%
With thionyl chloride at 0 - 40℃; for 6h;	98%
With thionyl chloride at 40℃; for 4h;	97%

: 153-94-6
D-tryptophan

: 496930-10-0
(R)-6-bromotryptophan

Conditions

Conditions	Yield
With oxygen; FAD-dependent tryptophan halogenase Thal; sodium bromide In isopropyl alcohol at 25℃; pH=7.4; Enzymatic reaction; chemoselective reaction;	100%
With sodium hypophosphate; recombinant phosphite dehydrogenase; recombinant tryptophan C-6 flavin-dependent halogenase tar14 from Streptomyces coelicolor CH999; recombinant tryptophan C-6 flavin-dependent reductase tar15 from Escherichia coli; nicotinamide adenine dinucleotide phosphate; flavin adenine dinucleotide; sodium chloride In aq. buffer at 30℃; pH=7.6; Enzymatic reaction; regiospecific reaction;
With alcohol dehydrogenase from Rhodococcus spp; flavin reductase PrnF from Pseudomonas fluorescens; tryptophan 6-halogenase Thal fromStreptomyces albogriseolus; NAD; oxygen; flavin adenine dinucleotide; sodium bromide In aq. phosphate buffer; isopropyl alcohol at 25℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;

: 76-05-1
trifluoroacetic acid

: 153-94-6
D-tryptophan

: C11H11BrN2O2*C2HF3O2

Conditions

Conditions	Yield
Stage #1: D-tryptophan With flavin adenine dinucleotide fully reduced neutral; NAD; oxygen; isopropyl alcohol; sodium bromide In aq. phosphate buffer at 25℃; pH=7.4; Enzymatic reaction; Stage #2: trifluoroacetic acid In acetonitrile	100%

: 120-57-0
piperonal

: 153-94-6
D-tryptophan

: C19H18N2O5

Conditions

Conditions	Yield
In acetonitrile at 20℃; Product distribution / selectivity; Inert atmosphere of nitrogen;	99.8%

: 67-56-1
methanol

: 153-94-6
D-tryptophan

: 4299-70-1, 7303-49-3, 22032-65-1
D-Tryptophan methyl ester

Conditions

Conditions	Yield
With sulfuric acid for 2h; Time; Reflux; Large scale;	99.4%
Stage #1: methanol; D-tryptophan With thionyl chloride for 18h; Reflux; Stage #2: With sodium carbonate	93%
With thionyl chloride at 10 - 45℃; for 2h; Large scale;	93.6%

: 153-94-6
D-tryptophan

: 552-30-7
trimellitic Anhydride

: (R)-2-(1-carboxy-2-(1H-indol-3-yl)ethyl)-1,3-dioxoisoindoline-5-carboxylic acid

Conditions

Conditions	Yield
In diethylene glycol dimethyl ether at 200℃; for 0.166667h; microwave irradiation;	99%

: 153-94-6
D-tryptophan

: 154-09-6, 526-53-4, 2899-29-8, 52485-52-6
(2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 15h; Inert atmosphere; Reflux;	98%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;	98%
With dimethyl sulfide borane In tetrahydrofuran Reflux;	92%

: 942130-82-7
(R)-1-benzotriazol-1-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropan-1-one

: 153-94-6
D-tryptophan

: (R)-3-(1H-indol-3-yl)-2-((R)-3,3,3-trifluoro-2-methoxy-2-phenylpropionylamino)propionic acid

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 20℃; for 12h;	98%

: 108-30-5
succinic acid anhydride

: 153-94-6
D-tryptophan

: (R)-N-[1-carboxy-2-(1H-indol-3-yl)ethyl]succinamic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 40h; Heating;	96%

: 96-22-0
pentan-3-one

: 153-94-6
D-tryptophan

: 1,1-diethyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; Pictet-Spengler reaction;	96%

: 100-52-7
benzaldehyde

: 153-94-6
D-tryptophan

: 888009-83-4
N-benzyl-D-tryptophan

Conditions

Conditions	Yield
With sodium cyanoborohydride In methanol	95%
With sodium cyanoborohydride In methanol at 20℃; for 24h;
Stage #1: benzaldehyde; D-tryptophan In methanol at 23℃; for 2h; Stage #2: With sodium cyanoborohydride In methanol at 0℃; for 15h;

: 501-53-1
benzyl chloroformate

: 153-94-6
D-tryptophan

: 2279-15-4
N-(benzyloxycarbonyl)-D-tryptophan

Conditions

Conditions	Yield
With sodium hydrogencarbonate; potassium carbonate In water; acetone at 30℃; for 3h; pH=8 - 10; Cooling with ice;	94%
With sodium hydroxide	88%
With sodium hydroxide	74%
With sodium hydroxide In water at 0 - 20℃;
Stage #1: D-tryptophan With sodium hydrogencarbonate; sodium carbonate In water; acetonitrile at 0℃; for 0.25h; pH=10 - Ca. 11; Cooling with ice; Stage #2: benzyl chloroformate In water; acetonitrile at 0 - 20℃; for 3h;

: 67-56-1
methanol

: 104-15-4
toluene-4-sulfonic acid

: 153-94-6
D-tryptophan

: (R)-2-Amino-3-(1H-indol-3-yl)-propionic acid methyl ester; compound with toluene-4-sulfonic acid

Conditions

Conditions	Yield
With p-toluenesulfonyl chloride at 75℃; for 4h;	94%
With p-toluenesulfonyl chloride for 20h; Heating;

...Expand

: 81-30-1
1,4,5,8-naphthalenetetracarboxylic dianhydride

: 153-94-6
D-tryptophan

: (R)-2-{7-[1-carboxy-2-(1H-indol-3-yl)ethyl]-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl}-3-(1H-indol-3-yl)propionic acid

Conditions

Conditions	Yield
With pyridine for 12h; Heating;	94%

: 616-38-6
carbonic acid dimethyl ester

: 153-94-6
D-tryptophan

: 4299-70-1, 7303-49-3, 22032-65-1
D-Tryptophan methyl ester

Conditions

Conditions	Yield
With sulfuric acid at 92℃; for 18h;	94%

: 67714-30-1
S-benzoyl-3-mercaptopropanoyl chloride

: 153-94-6
D-tryptophan

: 78818-49-2
N2-(S-benzoyl-3-mercaptopropanoyl)-D-tryptophan

Conditions

Conditions	Yield
With potassium carbonate In water	93%

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: 153-94-6
D-tryptophan

: (R)-2-(1,3-dioxooctahydroisoindol-2-yl)-3-(1H-indol-3-yl)propionic acid

Conditions

Conditions	Yield
With pyridine for 12h; Heating;	92%

: 610-14-0
2-nitrobenzyl chloride

: 153-94-6
D-tryptophan

: 1173180-35-2
(R)-3-(1H-indol-3-yl)-2-(2-nitrobenzamido)propanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0℃; Ionic liquid;	91%
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2h; Reagent/catalyst;	90%
With sodium hydroxide In tetrahydrofuran at 0℃; for 2h;	1.59 g

: 5616-32-0
(methylamino)acetonitrile

: 153-94-6
D-tryptophan

: C14H16N4O

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 5h; Solvent; Temperature;	91%

: 107-18-6
allyl alcohol

: 153-94-6
D-tryptophan

: H-D-Trp-OAll

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 25 - 95℃;	90.3%
With toluene-4-sulfonic acid In toluene at 25 - 95℃;	90%
With toluene-4-sulfonic acid In toluene at 25 - 95℃;	90.2%

: 407-25-0
trifluoroacetic anhydride

: 153-94-6
D-tryptophan

: 126689-19-8
4-(3-indolylmethyl)-2-trifluoromethyl-5(4H)-oxazolone

Conditions

Conditions	Yield
In diethyl ether at 30℃; for 0.166667h;	90%

: 97996-97-9
α-ethyl D-N-carbobenzoxyglutamate

: 153-94-6
D-tryptophan

: 1382326-14-8
Cbz-D-Glu(D-Trp-OH)-O-Et

Conditions

Conditions	Yield
Stage #1: α-ethyl D-N-carbobenzoxyglutamate With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Cooling with ice-water; Stage #2: D-tryptophan In N,N-dimethyl-formamide at 20℃; Cooling with ice-water; Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide Cooling with ice;	90%

: 100-44-7
benzyl chloride

: 153-94-6
D-tryptophan

: 141595-98-4
D-tryptophan benzyl ester

Conditions

Conditions	Yield
With Iron(III) nitrate nonahydrate; ammonia; sodium Reflux;	89%

: 120-57-0
piperonal

: 153-94-6
D-tryptophan

: 406938-39-4
(1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: piperonal; D-tryptophan With trifluoroacetic acid at 30 - 40℃; for 25h; Inert atmosphere; Stage #2: With hydrogenchloride In water at 40 - 50℃; for 17h; Temperature; Inert atmosphere;	88.5%

: 65706-99-2
1-benzyl N-carbobenzoxy-L-glutamate

: 153-94-6
D-tryptophan

: 1382326-04-6
Cbz-D-Glu(D-Trp-OH)-O-Bzl

Conditions

Yield

Stage #1: 1-benzyl N-carbobenzoxy-L-glutamate With 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Cooling with ice-water;
Stage #2: D-tryptophan In N,N-dimethyl-formamide at 20℃; for 6h; Cooling with ice-water;
Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide Product distribution / selectivity; Cooling with ice;

88%

: 81-84-5
1,8-Naphthalic anhydride

: 153-94-6
D-tryptophan

: 2-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-3-(1H-indol-3-yl)-propionic acid

Conditions

Conditions	Yield
In dimethyl sulfoxide at 150℃; for 0.5h;	87%

: 73167-00-7
2-Phenyl-iso-propyloxycarbonylfluorid

: 153-94-6
D-tryptophan

: 116246-59-4
Ppoc-D-Trp

Conditions

Conditions	Yield
With sodium hydroxide; sodium hydrogencarbonate In tetrahydrofuran; diethyl ether at 0℃; for 2h;	86%

: 24424-99-5
di-tert-butyl dicarbonate

: 153-94-6
D-tryptophan

: 5241-64-5
Boc-D-Trp-OH

Conditions

Conditions	Yield
With triethylamine In methanol Inert atmosphere;	86%
With sodium hydroxide In tetrahydrofuran; water at 0℃;

D(+)-Tryptophan Consensus Reports

Reported in EPA TSCA Inventory.

D(+)-Tryptophan Specification

The IUPAC name of D-Tryptophan is 2-amino-3-(1H-indol-3-yl)propanoic acid. With the CAS registry number 153-94-6, it is also named as (R)-a-Amino-3-indolepropionic Acid. The product's categories are Amino Acids Derivatives; Tryptophan [Trp, W]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids; Biochemistry; Indoles; Tryptophans; Chiral Compound; Amino Acids. It is white or yellow crystalline powder which is soluble in hot ethanol, alkali solution and water, insoluble in chloroform. In addition, this chemical is combustible, stable and incompatible with oxidizing agents. Besides, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.46; (4)ACD/LogD (pH 7.4): -1.46; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.697; (13)Molar Refractivity: 57.76 cm³; (14)Molar Volume: 149.8 cm³; (15)Polarizability: 22.9×10^-24 cm³; (16)Surface Tension: 71.1 dyne/cm; (17)Enthalpy of Vaporization: 74.44 kJ/mol; (18)Vapour Pressure: 8.3E-09 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 204.089878; (21)MonoIsotopic Mass: 204.089878; (22)Topological Polar Surface Area: 79.1; (23)Heavy Atom Count: 15; (24)Complexity: 245.

Preparation of D-Tryptophan: Using DL-tryptophan as raw materials, and adding chloroacetic anhydride to react in cooling condition. Grinding in ice water after sulfuric acid acidizing. Then filtering and recrystallizing in water. Finally, treating with pancreatic carboxypeptidase to remove the L-type. Then we can get the product by acetic acid acidification and ethanol recrystallization.

Uses of of D-Tryptophan: It can used in biochemistry research. And it is an important nutrient which is used as controlling agent of bark favus in medication.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)[C@H](N)Cc2c1ccccc1nc2
2. InChI:InChI=1/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	intraperitoneal	4289mg/kg (4289mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956.

Product Name

D(+)-Tryptophan

Synthetic route

D(+)-Tryptophan Consensus Reports

D(+)-Tryptophan Specification

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