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447439

Sigma-Aldrich

1-Methyl-L-tryptophan

95%, for peptide synthesis

Synonym(s):

(S)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid, L-(-)-1-Methyltryptophan

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O2
CAS Number:
21339-55-9
Molecular Weight:
218.25
MDL number:
MFCD00467133
UNSPSC Code:
12352209
PubChem Substance ID:
24868339
NACRES:
NA.22

product name

1-Methyl-L-tryptophan, 95%

Quality Level

100

Assay

95%

form

solid

optical activity

[α]24/D −8.0°, c = 2 in acetic acid

reaction suitability

reaction type: solution phase peptide synthesis

mp

242-245 °C (lit.)

application(s)

peptide synthesis

SMILES string

Cn1cc(C[C@H](N)C(O)=O)c2ccccc12

InChI

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

InChI key

ZADWXFSZEAPBJS-JTQLQIEISA-N

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Application

1-Methyl-L-tryptophan can be used:
  • In the preparation of L-tryptophan-based ligand for regioselective copper catalyzed N2-arylation of 1,2,3-triazoles.
  • As a key starting material for the total synthesis of (−)-ardeemin.
  • In the synthesis of cyclic peptide-capped gold nanoparticles as drug delivery systems.

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

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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Stefanie Siegert et al.
PloS one, 6(11), e27618-e27618 (2011-11-24)
Adaptive immune responses are initiated when T cells encounter antigen on dendritic cells (DC) in T zones of secondary lymphoid organs. T zones contain a 3-dimensional scaffold of fibroblastic reticular cells (FRC) but currently it is unclear how FRC influence
Cyclic peptide-capped gold nanoparticles as drug delivery systems.
Nasrolahi Shirazi A, et al.
Molecular Pharmaceutics, 10(2), 500-511 (2012)
Development of a L?Tryptophan?Based Ligand for Regioselective Copper Catalyzed N2?Arylation of 1, 2, 3?Triazoles.
Lopes A B, et al.
ChemistrySelect, 2(22), 6544-6548 (2017)
Jeroen F J Bogie et al.
Journal of neuroinflammation, 8, 85-85 (2011-07-26)
Multiple sclerosis (MS) is a chronic, inflammatory, demyelinating disease of the central nervous system (CNS) in which macrophages play a central role. Initially, macrophages where thought to be merely detrimental in MS, however, recent evidence suggests that their functional phenotype
Christiane A Opitz et al.
PloS one, 6(5), e19823-e19823 (2011-06-01)
1-methyl-D-tryptophan (1-D-MT) is currently being used in clinical trials in patients with relapsed or refractory solid tumors with the aim of inhibiting indoleamine-2,3-dioxygenase (IDO)-mediated tumor immune escape. IDO is expressed in tumors and tumor-draining lymph nodes and degrades tryptophan (trp)
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