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D-Tryptophan

D-Tryptophan structure

D-Tryptophan 

structure
  • CAS No:

    153-94-6

  • Formula:

    C11H12N2O2

  • Chemical Name:

    D-Tryptophan

  • Synonyms:

    D-Tryptophan;Tryptophan,D-;D-Tryptophane;(+)-Tryptophan;(R)-Tryptophan;(R)-α-Aminoindole-3-propanoic acid;(R)-α-Amino-3-indolepropionic acid;NSC 97942;(2R)-2-Amino-3-(1H-indol-3-yl)propanoic acid;(2R)-2-Azaniumyl-3-(1H-indol-3-yl)propanoate

  • Categories:

    Biochemical Engineering  >  Amino Acids and Proteins

Description

white powderChEBI: The D-enantiomer of tryptophan.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. D-tryptophan (Full name D (+)-Tryptophan) is a white to pale yellow or white crystalline powder at room temperature, odorless or slight odor, sligh


D(+)-tryptophan is a white solid. (NTP, 1992)|Solid


D(+)-tryptophan is a white solid. (NTP, 1992)|D-tryptophan is the D-enantiomer of tryptophan. It has a role as a bacterial metabolite. It is a tryptophan and a D-alpha-amino acid. It is a conjugate base of a D-tryptophanium. It is a conjugate acid of a D-tryptophanate. It is an enantiomer of a L-tryptophan. It is a tautomer of a D-tryptophan zwitterion.|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.

D-Tryptophan Basic Attributes

204.23

204.23

86198

205-819-9

7NS97N9H1G

97942

DTXSID0046989

29339990

Characteristics

79.1

-1.1

White to slightly yellow Powder

1.35 g/cm3

274 °C

50-70 °C

224.7±25.9 °C

31 ° (C=1, H2O)

H2O: 11 g/L (20 ºC)

Store at RT.

4.27E-07mmHg at 25°C

31.5 º (c=1, H2O 24 ºC)

142.6 Ų [M-H]-

Slightly soluble in water.

Salts, Acidic

Acidic salts, such as D(+)-TRYPTOPHAN, are generally soluble in water. The resulting solutions contain moderate concentrations of hydrogen ions and have pH's of less than 7.0. They react as acids to neutralize bases. These neutralizations generate heat, but less or far less than is generated by neutralization of inorganic acids, inorganic oxoacids, and carboxylic acid. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible. Many of these compounds catalyze organic reactions.

Safety Information

IRRITANT

NONH for all modes of transport

3

36/37/38-41-37/38-22

24/25-36/37/39-36-26

YN6129000

Xi

Stable. Incompatible with oxidizing agents.

Flash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)

Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Drug Information

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

D-Tryptophan Use and Manufacturing

Methods of Manufacturing

Using DL-tryptophan as raw material, add chloroacetic anhydride to react under cooling, acidify with sulfuric acid, grind in ice water, filter and recrystallize in water, and finally treat with pancreatic carboxypeptidase to remove L-type, acetic acid, ethanol Recrystallized and refined.

Uses

An essential amino acid found in naturally produced peptides. Unlike its stereoisomer, L-tryptophan, it is not used in structural or enzyme proteins.It is an important nutrient, used in medicine as a preventive agent for mangy.For biochemical research.

D-Tryptophan: ACTIVE

Computed Properties

Molecular Weight:204.22
XLogP3:-1.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:204.089877630
Monoisotopic Mass:204.089877630
Topological Polar Surface Area:79.1
Heavy Atom Count:15
Complexity:245
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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