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162698

Sigma-Aldrich

DL-Tryptophan

≥99% (HPLC), for peptide synthesis

Synonym(s):

(±)-α-Amino-3-indolepropionic acid, (±)-2-Amino-3-(3-indolyl)propionic acid, DL-3β-Indolylalanine

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About This Item

Empirical Formula (Hill Notation):
C11H12N2O2
CAS Number:
54-12-6
Molecular Weight:
204.23
Beilstein:
86199
EC Number:
200-194-9
MDL number:
MFCD00064339
UNSPSC Code:
12352209
PubChem Substance ID:
24850000
NACRES:
NA.22

product name

DL-Tryptophan, ≥99% (HPLC)

Quality Level

200

Assay

≥99% (HPLC)

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

mp

289-290 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

NC(Cc1c[nH]c2ccccc12)C(O)=O

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)

InChI key

QIVBCDIJIAJPQS-UHFFFAOYSA-N

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General description

DL-Tryptophan also known as 2-amino-3-(1H-indol-3-yl)-propionic acid, is commonly used in peptide synthesis.

Application

DL-Tryptophan is used as a starting material for the preparation of N-acyl monoisotripeptides via solution-phase peptide synthesis.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Solution-phase synthesis of chiral N-, O-, and S-acyl isopeptides
S Liaqat
Synthesis, 46, 67-72 (2014)
Aristeidis Chiotellis et al.
Molecular pharmaceutics, 11(11), 3839-3851 (2014-07-06)
As a continuation of our research efforts toward the development of tryptophan-based radiotracers for tumor imaging with positron emission tomography (PET), three new fluoroethoxy tryptophan analogues were synthesized and evaluated in vivo. These new tracers (namely, 4-(2-[(18)F]fluoroethoxy)-dl-tryptophan ([(18)F]4-FEHTP), 6-(2-[(18)F]fluoroethoxy)-dl-tryptophan ([(18)F]6-FEHTP)
Helen Ling et al.
Movement disorders : official journal of the Movement Disorder Society, 30(7), 960-967 (2015-04-10)
Glial cytoplasmic inclusions containing α-synuclein are the pathological hallmark of multiple system atrophy (MSA). Minimal change (MC-MSA) is an unusual MSA subtype with neuronal loss largely restricted to the substantia nigra and locus coeruleus. Immunohistochemistry on selected brain regions and
Kazuo Tatebayashi et al.
Nature communications, 6, 6975-6975 (2015-04-22)
The yeast high osmolarity glycerol (HOG) pathway activates the Hog1 MAP kinase, which coordinates adaptation to high osmolarity conditions. Here we demonstrate that the four-transmembrane (TM) domain protein Sho1 is an osmosensor in the HKR1 sub-branch of the HOG pathway.
C C K Hui et al.
Mucosal immunology, 8(5), 993-999 (2014-12-18)
Recent candidate gene and genome-wide association studies have identified "protective" associations between the single-nucleotide polymorphism (SNP) rs1837253 in the TSLP gene and risk for allergy, asthma, and airway hyperresponsiveness. The absence of linkage disequilibrium of rs1837253 with other SNPs in
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