20829-55-4

Basic information

• Product Name: CYCLO(-TRP-TRP)
• Synonyms: CYCLO(L-TRP-L-TRP);CYCLO(-TRP-TRP);(3S,6S)-3,6-Bis(indol-3-ylmethyl)-2,5-piperazinedione;Cyclo(L-tryptophanyl-L-tryptophanyl);Cyclo(L-Trp-L-Trp)≥ 98% (HPLC)
• CAS NO: 20829-55-4
• Molecular Formula: C₂₂H₂₀N₄O₂
• Molecular Weight: 372.42
• Mol File: 20829-55-4.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 813.4±60.0 °C(Predicted)
• Appearance: /
• Density: 1.364±0.06 g/cm3(Predicted)
• Storage Temp.: -15°C
• PKA: 12.86±0.60(Predicted)
• CAS DataBase Reference: CYCLO(-TRP-TRP)(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLO(-TRP-TRP)(20829-55-4)
• EPA Substance Registry System: CYCLO(-TRP-TRP)(20829-55-4)

Safety Data

• Hazardous Substances Data: 20829-55-4(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

Cyclo(L-Trp-L-Trp) is a tryptophan containing diketopiperazines isolated from the culture of the genetically engineered stain Actinosynnema pretiosum which shows moderate cytotoxic activities against HeLa PC3 lines;Also, it is derived from L-Tryptophan (T947210), which is an essential amino acid.

Upstream product

• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 17689-58-6 N-(benzyloxycarbonyl)-L-tryptophanyl-L-tryptophan methyl ester 
• 4299-70-1 L-tryptophan methyl ester 
• 4299-69-8 L-tryptophane benzyl ester 
• 73-22-3 L-Tryptophan 
• 81387-96-4 (S,S)-methyl 2-[2-amino-3-(indol-3-yl)propionylamino]-3-(indol-3-yl)propanoate 
• 13139-14-5 Boc-Trp-OH 
• 72254-56-9 (S,S)-methyl 2-[2-tert-butoxycarbonylamino-3-(indol-3-yl)-propionylamino]-3-(indol-3-yl)propanoate 

Downstream Products

• 73-22-3 L-Tryptophan 

Relevant articles and documents

The structure and conformation of the tryptophanyl diketopiperazines cyclo(Trp-Trp)·C2H6SO and cyclo(Trp-Pro)

The structure and conformation of the cyclic dipeptides [cyclo(L-Trp-L-Trp)·C2H6SO] and cyclo(L-Trp-L-Pro) have been investigated with X-ray crystallographic and spectroscopic methods. Cyclo(L-tryptophanyl-L-tryptophanyl)·DMSO solvate crystallized in the space group P212121 with cell dimensions a = 6.193(2), b = 11.545(3), c = 31.117(4) A. The crystal structure is stabilized by four hydrogen bonds (three intermolecular hydrogen bonds and one intramolecular bond). The first intermolecular bond is between the oxygen of DMSO and the nitrogen of indole ring 2, in contrast to the second intramolecular hydrogen bond between the nitrogen of indole ring 1 and the oxygen of DMSO. The two remaining intermolecular hydrogen bonds are between the nitrogens of the DKP ring and the carbonyl oxygens of the DKP ring. The values of X1A1 (-45.764) and X1A2 (67.437) indicate an extended side chain conformation for Trp residue 1 (EN) and a folded conformation for Trp residue 2. The DKP ring is more planar than in other cyclic dipeptide compounds (φ1 = 11.414, ψ1 = -7.516, φ2 = 12.471, and ψ2 = -8.256). In cyclo(L-Trp-L-Trp) the Cβ resonance of L-tryptophan (29.88 ppm) is shifted upfield 0.82 ppm when compared with the same resonance in cyclo(L-Trp-L-Gly) (30.7 ppm) and cyclo(L-Leu-L-Trp) (30.7 ppm). Two conformations of cyclo(Trp-Pro) crystallized in the space group P1 with cell dimensions a = 5.422(1), b = 9.902(1), c = 13.443(2) A, α = 80.42(1), β = 78.61(1), and γ = 89.13(1)°. The conformation of the backbone and the orientation of the aromatic side chains for these conformers are very similar. The DKP rings for both conformers adopt a typical boat conformation in contrast to the flattened chair conformation observed for cyclo(Tyr-Pro) and cyclo(Phe-F-Pro). The tryptophan side chains of these conformers are folded towards the diketopiperazine (DKP) ring. The pyrrolidine ring for conformer 1 can be described as an envelope (Cs-Cβ-endo) conformation in contrast to the pyrrolidine ring symmetry for conformer 2 which is an intermediate between Cs and C2 rather than pure Cs for the proline ring with Cβ-endo and Cγ-exo with respect to C′. The two prolyl rings are puckered at the β-carbon atoms which deviate from the best planes defined by the four remaining atoms. The crystal structures are stabilized by four intermolecular hydrogens bonds. An intermolecular bond between the nitrogen of the indole ring (conformer 1) and the carbonyl oxygen of the DKP ring (conformer 2) was observed. The second hydrogen bond is between the nitrogen of the indole ring (conformer 2) and the carbonyl oxygen of the DKP ring (conformer 1). The last two hydrogens involve the carbonyl oxygens of the DKP rings and the nitrogens of the DKP rings [carbonyl oxygen of DKP ring (conformer 1) - nitrogen of DKP ring (conformer 2); nitrogen of DKP ring (conformer 1) - carbonyl oxygen of DKP ring (conformer 2)].

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Three types of induced tryptophan optical activity compared in model dipeptides: Theory and experiment

The tryptophan (Trp) aromatic residue in chiral matrices often exhibits a large optical activity and thus provides valuable structural information. However, it can also obscure spectral contributions from other peptide parts. To better understand the indu

Investigation of reaction mechanism of amino acids and phosphorus trichloride by 31P NMR and ESI-MS/MS

The reaction of amino acids and phosphorus trichloride in THF was studied by 31P NMR tracing and ESI-MS/MS. A series of hydridophoranes and cyclic dipeptides were obtained. The reaction presented interesting diversity and the reaction mechanism was proposed. The mechanism suggests that phosphorus plays an important role in the synthesis of amino acid hydridophorane and cyclic dipeptides. The results also show that 31P NMR and ESI-MS/MS are useful tools for the investigation of reaction mechanism. Copyright