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364517

Sigma-Aldrich

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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¥3,820
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¥12,000

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5 G
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25 G
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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2 · HCl
CAS Number:
7524-52-9
Molecular Weight:
254.71
Beilstein:
4240280
EC Number:
231-385-5
MDL number:
MFCD00066134
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24862436
NACRES:
NA.22

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Product Name

L-Tryptophan methyl ester hydrochloride, 98%

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

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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.[1]
  • Tadalafil (Cialis), a type-V phosphodiesterase (PDE5) inhibitor.[2]
  • Isoroquefortine C.[3]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

364517-25G:
364517-BULK:
364517-5G:
364517-VAR:

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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
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)
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.
Christopher Jonathan Daraius Austin et al.
Amino acids, 39(2), 565-578 (2010-02-09)
The first step in the kynurenine pathway of tryptophan catabolism is the cleavage of the 2,3-double bond of the indole ring of tryptophan. In mammals, this reaction is performed independently by indoleamine 2,3-dioxygenase-1 (IDO1), tryptophan 2,3-dioxygenase (TDO) and the recently
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