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364517

L-Tryptophan methyl ester hydrochloride

Name: <SC>L</SC>-Tryptophan methyl ester hydrochloride
Brand: ALDRICH

98%, for peptide synthesis

Synonym(s):

(S)-Tryptophan methyl ester hydrochloride, H-(L)-Trp-OMe hydrochloride, L-(-)-Tryptophan methyl ester hydrochloride, Tryptophan methyl ester hydrochloride

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About This Item

Empirical Formula (Hill Notation):

C₁₂H₁₄N₂O₂ · HCl

CAS Number:

7524-52-9

Molecular Weight:

254.71

NACRES:

NA.22

PubChem Substance ID:

24862436

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

231-385-5

MDL number:

MFCD00066134

Beilstein/REAXYS Number:

4240280

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Properties

Product Name

L-Tryptophan methyl ester hydrochloride, 98%

Quality Level

100

assay

98%

optical activity

[α]20/D +18°, c = 5 in methanol

reaction suitability

reaction type: solution phase peptide synthesis

mp

218-220 °C (lit.)

application(s)

peptide synthesis

SMILES string

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

InChI

1S/C12H14N2O2.ClH/c1-16-12(15)10(13)6-8-7-14-11-5-3-2-4-9(8)11;/h2-5,7,10,14H,6,13H2,1H3;1H/t10-;/m0./s1

InChI key

XNFNGGQRDXFYMM-PPHPATTJSA-N

Description

Application

L-Tryptophan methyl ester hydrochloride can be used as a reactant to prepare:

Oxamoyl derivatives of N-(2-aminobenzoyl)-L-tryptophan (dipeptides) by acylation reaction with 3,1-benzoxazinones.
Tadalafil (Cialis), a type-V phosphodiesterase (PDE5) inhibitor.
Isoroquefortine C.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Synthesis of tadalafil (Cialis) from L-tryptophan

Xiao Sen, et al.

Tetrahedron Asymmetry, 20(18), 2090-2096 (2009)

Acyl substrate preferences of an IAA-amido synthetase account for variations in grape (Vitis vinifera L.) berry ripening caused by different auxinic compounds indicating the importance of auxin conjugation in plant development.

Christine Böttcher et al.

Journal of experimental botany, 62(12), 4267-4280 (2011-05-06)

Nine Gretchen Hagen (GH3) genes were identified in grapevine (Vitis vinifera L.) and six of these were predicted on the basis of protein sequence similarity to act as indole-3-acetic acid (IAA)-amido synthetases. The activity of these enzymes is thought to

Synthesis of acyl derivatives of L-tryptophan containing residues of anthranilic and oxalic acids

Shemchuk LA, et al.

Russ. J. Org. Chem., 44(5), 693-696 (2008)

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Global Trade Item Number

SKU	GTIN
364517-25G	04061832642000
364517-5G	04061831825381