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Merck
CN

364517

L-Tryptophan methyl ester hydrochloride

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

Key Documents

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Product Name

L-Tryptophan methyl ester hydrochloride, 98%

InChI key

XNFNGGQRDXFYMM-PPHPATTJSA-N

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

SMILES string

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

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

Quality Level

100

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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.

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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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0890
STBL1997
STBK5073
STBK0690
STBJ5734

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Synthesis of tadalafil (Cialis) from L-tryptophan
Xiao Sen, et al.
Tetrahedron Asymmetry, 20(18), 2090-2096 (2009)
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
Bruno M Schiavi et al.
The Journal of organic chemistry, 67(3), 620-624 (2002-02-22)
A short and efficient total synthesis of isoroquefortine C, the 3,12-(Z)-isomer of roquefortine C, from L-tryptophan methyl ester hydrochloride and 4(5)-(hydroxy)methylimidazole hydrochloride is described.
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)
Patrick P C Boor et al.
European journal of immunology, 41(6), 1663-1674 (2011-04-07)
Allo-reactive memory T cells are a major barrier for induction of immunological tolerance to allografts in humans. Here, we report that stimulation of unfractionated human T cells with TLR-stimulated allogeneic plasmacytoid dendritic cells (pDCs) induces CD8(+) regulatory T cells (Tregs)
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