Didemnin B

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Product Name: Didemnin B
CAS No.: 77327-05-0
Chemical Name: Didemnin B
Synonyms: Didemnin B;Didemnin A, N-[1-[(2S)-2-hydroxy-1-oxopropyl]-L-prolyl]-;N-(L-Lac-L-Pro-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-3-oxohexanoyl]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-]
CBNumber: CB51247302
Molecular Formula: C57H89N7O15
Formula Weight: 1112.36
MOL File: 77327-05-0.mol

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Didemnin B Property

Boiling point:: 821.94°C (rough estimate)
Density: 1.0596 (rough estimate)
refractive index: 1.6910 (estimate)
storage temp.: Store at -20°C
solubility: Acetonitrile: 1 mg/ml
form: A crystalline solid
pka: 11.28±0.70(Predicted)
color: White to off-white
optical activity: -82.0622 (CHCl3)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

American Custom Chemicals Corporation

Product number: API0028325
Product name: DIDEMNIN B
Purity: 95.00%
Packaging: 5MG
Price: $458.64
Updated: 2021/12/16

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Didemnin B Chemical Properties,Usage,Production

Description

Didemnin B is a cyclic depsipeptide extracted from the Caribbean tunicate Trididemnum cyanophorum. Didemnin B activates caspase, inducing apoptosis and preventing eukaryotic elongation factor 2 (eEF-2)-dependent translocation, inhibiting protein synthesis. This agent also has immunosuppressive and antiviral properties. It is an effective immunosuppressive agent. It is approximately 1,000 times more effective than the standard cyclosporin A. Further study may prove it useful in repressing rejections of transplanted organs[1].

Definition

ChEBI: A natural product found particularly in Lyngbya majuscula and Trididemnum solidum.

Biological Activity

Didemnin B belongs to a group of cyclic depsipeptides produced by Trididemnum solidum Van Name and provides a unique lactylprolin unit in the side chain of the molecule. The natural product interacts with the 80S ribosome, thereby retaining eEF1α in the ribosomal complex despite exhibiting proper GTP hydrolysis. Consequently, eEF2 binding to the ribosome and subsequent eEF2-dependent tRNA translocation are prevented. Didemnin B only shows sufficient binding affinity to the ribosome-eEF1α-complex and not to eEF1α alone. The natural product has antiviral properties and is cytotoxic against both cancerous and normal mammalian cells, whereby highly proliferating cells are more strongly affected than resting cells[2].

in vitro

Didemnin B has activity against miirine B16 melanoma, P388 leukemia, and M5076 sarcoma.

in vivo

Didemnin B is a potent inhibitor of L1210 growth.

References

[1] Renneberg, R. Viola Berkling and V. Loroch. “Chapter 7 – Green Biotechnology.”Biotechnology for Beginners (Third Edition) (2023): 241-290.
[2] Luisa D. Burgers , Robert Fürst. “Natural products as drugs and tools for influencing core processes of eukaryotic mRNA translation.” Pharmacological research 170 (2021): Article 105535.

Didemnin B Preparation Products And Raw materials

Raw materials

Preparation Products

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77327-05-0, Didemnin BRelated Search:

AC-ALA-ALA-PHE-OME AC-2-METHOXY-PHE-OET L-ALANYL-L-ALANYL-L-ALANINE METHYL ESTER ACETATE Pareptide H-PRO-TYR-OH AC-TYR(ME)-OH Ethyl N-acetyl-L-tyrosinate hydrate AC-TYR(ME)-OME (D-LEU2)-MELANOCYTE-STIMULATING HORMONE-RELEASE INHIBITING FACTOR (S)-2-Amino-3-(4-methoxyphenyl)propionicacidethylester Didemnin B

Didemnin B

N-(L-Lac-L-Pro-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-3-oxohexanoyl]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-]

Didemnin A, N-[1-[(2S)-2-hydroxy-1-oxopropyl]-L-prolyl]-

77327-05-0

C57H89N7O15