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Merck
CN

T90204

L-Tryptophan

99%

Synonym(s):

(S)-2-Amino-3-(3-indolyl)propionic acid, L-α-Amino-3-indolepropionic acid

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
73-22-3
Molecular Weight:
204.23
EC Number:
200-795-6
UNSPSC Code:
12352209
MDL number:
MFCD00064340
Beilstein/REAXYS Number:
86197

Key Documents

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InChI

1S/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-/m0/s1

InChI key

QIVBCDIJIAJPQS-VIFPVBQESA-N

SMILES string

N[C@@H](Cc1c[nH]c2ccccc12)C(O)=O

assay

99%

optical activity

[α]20/D −31.5°, c = 1 in H2O

optical purity

ee: 99% (GLC)

mp

280-285 °C (dec.) (lit.)

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Application

Employed in the synthesis of bridged indole alkaloids.

Other Notes

Amino acid precursor of serotonin and melatonin

Storage Class

13 - Non Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
00923PV
00430TP
00401PV
18721PO
18502KN

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Journal of the Chemical Society. Chemical Communications, 1559-1559 (1994)
Claudia Temperini et al.
Bioorganic & medicinal chemistry, 16(18), 8373-8378 (2008-09-09)
An activation study of mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms I-XIV with D- and L-tryptophan has been performed both by means of kinetic and X-ray crystallographic techniques. These compounds show a time dependent activity against isozyme CA II, with
Rafat M Mohareb et al.
Bioorganic & medicinal chemistry, 19(9), 2966-2974 (2011-04-16)
There is a great deal of interest in neurotrophin therapy to prevent neuronal degeneration. The present study aimed at synthesizing new functionalized indole derivatives with structures justifying neuroprotective activity using L-tryptophan (TRP) as starting material. The potential neuroprotective effect of
Eduard Dolusić et al.
Journal of medicinal chemistry, 54(15), 5320-5334 (2011-07-06)
Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase
Huixi Zou et al.
Journal of natural products, 72(1), 44-52 (2008-12-31)
This study reports that a series of tryptophan derivatives with modifications on the side chain or at the indole ring were accepted by two cyclic dipeptide prenyltransferases, CdpNPT and FtmPT1, and converted to prenylated derivatives. The structures of the enzymatic
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