Description Description Characteristics and Functions Project Standards Application References References
ChemicalBook > CAS DataBase List > D-Tryptophan

D-Tryptophan

Description Description Characteristics and Functions Project Standards Application References References
Product Name
D-Tryptophan
CAS No.
153-94-6
Chemical Name
D-Tryptophan
Synonyms
D-TRYPTOPHAN;D-TRP;H-D-TRP-OH;LTR;D-Trp-OH;WV;D-Triptophan;D-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID;TRP-01;(S)-alph
CBNumber
CB2280905
Molecular Formula
C11H12N2O2
Formula Weight
204.23
MOL File
153-94-6.mol
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D-Tryptophan Property

Melting point:
282-285 °C (dec.)(lit.)
alpha 
31.5 º (c=1, H2O 24 ºC)
Boiling point:
342.72°C (rough estimate)
Density 
1.1754 (rough estimate)
refractive index 
31 ° (C=1, H2O)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Aqueous Base (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
pka
2.30±0.10(Predicted)
form 
Powder
color 
White to slightly yellow
Water Solubility 
11 g/L (20 ºC)
BRN 
86198
Stability:
Stable. Incompatible with oxidizing agents.
InChIKey
QIVBCDIJIAJPQS-SECBINFHSA-N
LogP
0.704 (est)
CAS DataBase Reference
153-94-6(CAS DataBase Reference)
EPA Substance Registry System
D-Tryptophan (153-94-6)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38-41-37/38-22
Safety Statements 
24/25-36/37/39-36-26
WGK Germany 
3
RTECS 
YN6129000
F 
8
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29339990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T9753
Product name
D-Tryptophan
Purity
≥98.0% (HPLC)
Packaging
1g
Price
$22.7
Updated
2024/03/01
Sigma-Aldrich
Product number
T9753
Product name
D-Tryptophan
Purity
≥98.0% (HPLC)
Packaging
5g
Price
$57.9
Updated
2024/03/01
TCI Chemical
Product number
T0539
Product name
D-Tryptophan
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$30
Updated
2024/03/01
TCI Chemical
Product number
T0539
Product name
D-Tryptophan
Purity
>98.0%(HPLC)(T)
Packaging
25g
Price
$112
Updated
2024/03/01
Alfa Aesar
Product number
A18426
Product name
D-Tryptophan, 99%
Packaging
5g
Price
$38.2
Updated
2024/03/01
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D-Tryptophan Chemical Properties,Usage,Production

Description

D(+)-tryptophan is the D-form (non-proteinogenic form) of the amino acid tryptophan. It can be used for Human embryonic kidney cell (HEK-293, ATCC: CRL-1573) culture. It is also a sweetener used to study the release of incretins from enteroendocrine cells triggered by sugar but not by sweeteners.

Description

D-tryptophan (Full name D (+)-Tryptophan) is a white to pale yellow or white crystalline powder at room temperature, odorless or slight odor, slightly sweet taste. Solubility in water is 1.14 g (25 ℃), soluble in dilute acid and alkali, stable in alkali, decomposed in strong acid, slightly soluble in ethanol, not soluble in chloroform, ethyl ether. It plays an important role for human and animal growth and development, metabolism, known as the second essential amino acids. They are almost identical with L-type and physical and chemical properties, and only the optical activity is opposite. But their distribution, function and coenzyme have diversity. Its melting point is very high, generally above 200 degrees. It can dissolve in water, and in the near UV region it has the ability to absorb light.
Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG. the D-stereoisomer is occasionally found in naturally produced peptides (for example, the marine venom peptide contryphan). The distinguishing structural characteristic of tryptophan is that it contains an indole functional group. It is an essential amino acid as defined by its growth effects on rats.

Characteristics and Functions

D-tryptophan amino acid, as a non-reactive protein, has special physiological properties. It can be used as a non-nutritive sweeteners, feed additive, plant growth agents in food feed industry and agriculture. In the pharmaceutical industry, it mainly used for the synthesis of various polypeptides, instead of L-tryptophan peptide drug for half-life extending and reduce the side effects, but it will not resistant to the front body, and it will become important enzyme inhibitor. It can also improve the body's immunity, delayed allergic reactions. Most peptide antibiotic can resistant gram-positive bacteria, Gram-negative bacteria and some, such as Pseudomonas aeruginosa, mycobacteria, fungi, bacteria, pathogens and tumor cells, which have better inhibit and kill ability.
D-tryptophan can be used for the synthetic of semi-synthetic antibiotics, for which pharmacological plays an important role for the side chain. The peptide bond is difficult to be β-lactam enzyme action, thus high stability, and has broad antibacterial spectrum, toxicity, hypoallergenic, rapid absorption, high blood concentrations of the drug long duration.

Project Standards

Appearance  white or slightly yellow crystalline powder
Content 99.0%~101.0%
Specific rotation [α] D20 + 30.5 °~+ 32.5 °
Transmittance ≥95.0%
Acidity PH 5.5~6.4
Loss on drying ≤0.2%
Residue on ignition ≤0.1%
Chloride [Cl-] ≤0.02%
Sulphate [SO42-] ≤0.02%
Ammonium [NH4 +] ≤0.02%
Heavy metals [Pb] ≤10ppm
Ferric [Fe] ≤10ppm
Arsenic salt [As2O3] ≤1ppm
Other amino acids compliance

Application

An important nutrient, niacin is used as the control agent Medicine
Production method: D-tryptophan as raw material, chloroacetic anhydride was added under cooling state after polishing sulfuric acid in ice water, filtered and recrystallized from water, and finally treatment with carboxypeptidase trypsin to remove L-type, acidified with acetic acid, ethanol recrystallization refining.

References

https://pubchem.ncbi.nlm.nih.gov/compound/D-Tryptophan#section=Top

References

Fujita, Yukihiro, et al. "Incretin release from gut is acutely enhanced by sugar but not by sweeteners in vivo." American Journal of Physiology Endocrinology & Metabolism 296.3(2009):E473.
Bacchus, W, W. Weber, and M. Fussenegger. "Increasing the dynamic control space of mammalian transcription devices by combinatorial assembly of homologous regulatory elements from different bacterial species." Metabolic Engineering 15.1(2013):144.

Chemical Properties

white powder

Uses

An essential amino acid found in naturally produced pedtides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins.

Uses

D-Tryptophan is used for human embryonic kidney cell (HEK-293, ATCC: CRL-1573) culture. The product is a sweetener used to study the release of incretins from enteroendocrine cells triggered by sugar but not by sweeteners.

Definition

ChEBI: The D-enantiomer of tryptophan.

General Description

White solid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Fire Hazard

Flash point data are not available for D(+)-Tryptophan, but D(+)-Tryptophan is probably combustible.

Biochem/physiol Actions

Low level of D-tryptophan is capable of preventing the growth of an?L-tryptophan-requiring mutant of the?E. coli.

D-Tryptophan Preparation Products And Raw materials

Raw materials

Chloroacetic anhydride DL-Tryptophan

Preparation Products

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View Lastest Price from D-Tryptophan manufacturers

HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
D(+)-Tryptophan 153-94-6
Price
US $100.00-75.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000Ton
Release date
2024-08-13
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
D(+)-Tryptophan 153-94-6
Price
US $55.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-06-03
WUHAN FORTUNA CHEMICAL CO., LTD
Product
D(+)-Tryptophan 153-94-6
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98%min
Supply Ability
500kgs
Release date
2021-08-27

153-94-6, D-TryptophanRelated Search:

L-Alanine ALTRENOGEST Tris(hydroxymethyl)aminomethane α-Lipoic Acid 6-Aminocaproic acid Propionic acid Glycine L-Tryptophan D(-)-Glutamic acid D-Valine D-Alanine (1S,3S)-1-(1,3-Benzodioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic Acid Methyl Ester 2-Hydroxypropyl Nortadalafil Tadalafil EP Impurity N-Octyl Nortadalafil (1S,3R)-1-Benzo[1,3]dioxol-5-yl-2-(2-chloro-acetyl)-2,3,4,9-tetrahydro-1H-b-carboline-3-carboxylic Acid Methyl Ester 1,1'-Ethylidenebis(tryptophan) (1R,3R)-2-acetyl-1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro- 1H-pyrido[3,4-b]indole-3-carboxylate

  • D-TRP
  • D(+)-TRYPTOPHAN
  • D-TRYPTOPHAN
  • D-TRYPTOPHANE
  • D-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID
  • D-2-AMINO-3-INDOLEPROPIONIC ACID
  • D-2-AMINO-3-INDOLYLPROPANOIC ACID
  • D-ALPHA-AMINO-3-INDOLEPROPIONIC ACID
  • D-A-AMINO-3-INDOLEPROPIONIC ACID
  • D-Triptophan
  • D-TRYPTOPHAN, 99+% (99% EE/GLC)
  • D-TRYPTOPHAN, H-D-TRP-OH
  • D-TRYTOPHAN
  • D(+)-Tryptophan, 99+%
  • H-D-TRP-OH USP24 (IN BULK QUANTITY)
  • TRYPTOPHAN, D-(RG)
  • (R)-a-Amino-3-indolepropionic acid
  • (R)-a-Aminoindole-3-propanoic acid
  • D-Tryptophan (9CI)
  • NSC 97942
  • Tryptophan, D- (8CI)
  • D-TRYPTOPHAN, =98.0% (HPLC)
  • WV
  • D-Tryptophan≥ 99% (Assay)
  • FREE SAMPLE NCV D-TRYPTOPHAN
  • H-D-Trp-OH (R)-2-Amino-3-(3-indolyl)propionic acid D-α-Amino-3-indolepropionic acid 3,3'-Indolyl-2-alanine
  • D-Tryptophan,99%e.e.
  • (R)-2-Amino-3-(3-indolyl)propionic acid~H-D-Trp-OH
  • D-Tryptophane, (R)-2-Amino-3-(3-indolyl)propionic acid, D-a-Amino-3-indolepropionic acid
  • (2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
  • (αR)-α-Amino-1H-indole-3-propanoic acid
  • D-Trp-OH
  • (R)-2-Amino-3-(1H-indol-3-yl)-propanoic acid
  • D-tyrptophan
  • (R)-2-Amino-3-(3-indolyl)propionic acid, D-α-Amino-3-indolepropionic acid
  • D-Tryptophan,(R)-2-Amino-3-(3-indolyl)propionic acid, D-α-Amino-3-indolepropionic acid
  • D-B-3-INDOLYLALANINE
  • H-D-TRP-OH
  • H-D-TYP-OH
  • 3,3'-indolyl-2-alanine
  • (R)-(+)-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID
  • (R)-2-AMINO-3-(3-INDOLYL)PROPIONIC ACID
  • (r)-alpha-amino-3-indolepropionicacid
  • (r)-alpha-aminoindole-3-propanoicacid
  • (r)-tryptophan
  • D-α-Amino-3-indolepropionic acid
  • D-β-3-Indolyl alanine
  • (S)-alph
  • (S)-alpha-Amino-beta-indolepropionic acid
  • (S)-Tryptophan 1H-Indole-3-alanine, (S)-
  • d-tryptopha
  • TRYPTOPHAN, D-
  • D-Tryptophan-d5
  • D(+)-Tryptophan, 99+% 25GR
  • D(+)-Tryptophan, 99+% 5GR
  • (R)-α-AMino-3-indolepropionic Acid
  • (R)-α-AMinoindole-3-propanoic Acid
  • (2S)-2-amino-3-(1H-indol-3-yl)propionic acid