Basic information Description Description Characteristics and Functions Project Standards Application References References Safety Supplier Related
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D(+)-Tryptophan

Basic information Description Description Characteristics and Functions Project Standards Application References References Safety Supplier Related

D(+)-Tryptophan Basic information

Product Name:
D(+)-Tryptophan
Synonyms:
  • 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
CAS:
153-94-6
MF:
C11H12N2O2
MW:
204.23
EINECS:
205-819-9
Product Categories:
  • tadalafil intermediate
  • Intermediate of Tadalafil
  • Amino Acids & Derivatives
  • Aromatics
  • Heterocycles
  • Isotope Labelled Compounds
  • Amino Acid Derivatives
  • Tryptophan [Trp, W]
  • Amino Acids and Derivatives
  • alpha-Amino Acids
  • Amino Acids
  • Biochemistry
  • Indoles
  • Indole Derivatives
  • Amino Acids Derivatives
  • Tryptophans
  • Chiral Compound
  • Amino Acids
  • Thiophenes
  • 1
Mol File:
153-94-6.mol
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D(+)-Tryptophan Chemical Properties

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
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
CAS DataBase Reference
153-94-6(CAS DataBase Reference)
EPA Substance Registry System
D-Tryptophan (153-94-6)
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Safety Information

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
8
TSCA 
Yes
HazardClass 
IRRITANT
HS Code 
29339990

MSDS

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D(+)-Tryptophan Usage And Synthesis

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

An essential amino acid found in naturally produced peptides. 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

D(+)-TryptophanSupplier

Shanghai Hanhong Scientific Co.,Ltd. Gold
Tel
;021-54306202- ;
Email
jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com
Products Intro
Product Name:D-Tryptophan
CAS:153-94-6
Purity:99%
Nanjing Redwood Fine Chemical Co., Ltd. Gold
Tel
86-400-8464006
Email
tony@redwoodchem.com
Products Intro
Product Name:D-Tryptophan
CAS:153-94-6
Purity:98% HPLC Package:1t 500kg 100kg 5kg 1kg
Shanghai SE Pharm Co., Ltd Gold
Tel
;021-50800327-
Email
sales4@sepharm.com.cn;sales2@sepharm.com.cn
Products Intro
Product Name:D(+)-Tryptophan
CAS:153-94-6
Purity:0.99 Package:10ASSAYS/month
Jiangsu United-value International Trading Co., Ltd. Gold
Tel
0519-89885611 89885616 15312500313
Email
luke.li@uvcs.cn.com
Products Intro
Product Name:D(+)-Tryptophan
CAS:153-94-6
Package:500g;1kg;10kg
Wuxi Bikang Bioengineering Co., Ltd Gold
Tel
0510-80245888-
Email
1258079079@qq.com
Products Intro
Product Name:D-Tryptophan
CAS:153-94-6
Purity:99 Package:25KG