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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)

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.

Storage Class Code

11 - Combustible Solids

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)
Mariano Soiza-Reilly et al.
Neuropharmacology, 89, 185-192 (2014-09-28)
5-HT1A receptors are widely expressed in the brain and play a critical role in feedback inhibition of serotonin (5-HT) neurons through multiple mechanisms. Yet, it remains poorly understood how these feedback mechanisms, particularly those involving long-range projections, adapt in mood
Sonia Aguila et al.
PloS one, 9(12), e114454-e114454 (2014-12-09)
The inefficient glycosylation of consensus sequence on N135 in antithrombin explains the two glycoforms of this key anticoagulant serpin found in plasma: α and β, with four and three N-glycans, respectively. The lack of this N-glycan increases the heparin affinity
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
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