478183-57-2

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-3-CHLORO-D-TYROSINE is used as a building block for the synthesis of peptides and other organic molecules, contributing to the development of new pharmaceuticals. Its specific properties and structure enable the creation of innovative drug compounds with potential therapeutic applications.
Used in Medicinal Chemistry Research:
N-BOC-3-CHLORO-D-TYROSINE is employed as a key component in the study of medicinal chemistry, providing valuable insights into the design and development of novel pharmaceuticals. Its synthesis and analysis can aid in understanding the properties and interactions of various compounds, facilitating the advancement of drug discovery processes.
Used in Drug Discovery:
N-BOC-3-CHLORO-D-TYROSINE is utilized as a crucial element in drug discovery, playing a significant role in the identification and development of new therapeutic agents. Its unique structure and properties allow for the exploration of various chemical modifications and interactions, leading to the discovery of potential drug candidates with improved efficacy and safety profiles.

InChI:InChI=1/C14H18ClNO5/c1-14(2,3)21-13(20)16-10(12(18)19)7-8-4-5-11(17)9(15)6-8/h4-6,10,17H,7H2,1-3H3,(H,16,20)(H,18,19)/t10-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 162599-96-4 3-chloro-D-tyrosine 
• 556-02-5 tyrosine 

Downstream Products

• 162465-44-3 methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-(3-chloro-4-methoxyphenyl)propanoate 
• 905309-57-1 methyl (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoate 
• 905309-58-2 (2R)-2-(acryloylamino)-3-(3-chloro-4-methoxyphenyl)propanoic acid 
• 905309-67-3 allyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate 
• 905309-74-2 (3S,10R,16S)-16-[(2Z)-2-bromo-3-phenylprop-2-enyl]-10-(3-chloro-4-methoxybenzyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone 
• 905309-81-1 (3S,10R,16R)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone 
• 905309-75-3 (3S,10R,16S)-10-(3-chloro-4-methoxybenzyl)-16-[(2Z)-3-iodo-3-phenylprop-2-enyl]-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone 
• 905309-76-4 (1S,3Z)-1-allyl-3-bromo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate 
• 905309-82-2 (1R,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate 
• 905309-77-5 (1S,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate 
• 905309-72-0 (3S,10R,16S)-16-[(2Z)-2-benzylidene-4-phenylbut-3-ynyl]-10-(3-chloro-4-methoxybenzyl)-3-isobutyl-6,6-dimethyl-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone 
• 704870-54-2 methyl (2R)-2-amino-3-(3-chloro-4-methoxyphenyl)propanoate 

Relevant academic research and scientific papers

Cryptophycin-55/52 based antibody-drug conjugates: Synthesis, efficacy, and mode of action studies

Cryptophycin-52 (CR52), a tubulin inhibitor, exhibits promising antitumor activity in vitro (picomolar level) and in mouse xenograft models. However, the narrow therapeutic window in clinical trials limits its further development. Antibody-drug conjugate (ADC), formed by coupling cytotoxic compound (payload) to an antibody via a linker, can deliver drug to tumor locations in a targeted manner by antibody, enhancing the therapeutic effects and reducing toxic and side effects. In this study, we aim to explore the possibility of CR52-based ADC for tumor targeted therapy. Due to the lack of a coupling site in CR52, its prodrug cryptophycin-55 (CR55) containing a free hydroxyl was synthesized and conjugated to the model antibody trastuzumab (anti-HER2 antibody drug approved by FDA for breast cancer therapy) via the linkers based on Mc-NHS and Mc-Val-Cit-PAB-PNP. The average drug-to-antibody ratios (DARs) of trastuzumab-CR55 conjugates (named T-L1-CR55, T-L2-CR55, and T-L3-CR55) were 3.50, 3.29, and 3.35, respectively. These conjugates exhibited potent cytotoxicity in HER2-positive tumor cell lines with IC50 values at low nanomolar levels (0.58–1.19 nM). Further, they displayed significant antitumor activities at the doses of 10 mg/kg in established ovarian cancer (SKOV3) and gastric cancer (NCI–N87) xenograft models without overt toxicities. Finally, the drug releases were analyzed and the results indicated that T-L3-CR55 was able to effectively release CR55 and further epoxidized to CR52, which may be responsible for its best performance in antitumor activities. In conclusion, our results demonstrated that these conjugates have the potential for tumor targeted therapy, which provides insights to further research the CR55/CR52-based ADC for tumor therapy.

Total synthesis of cryptophycin analogues via a scaffold approach

Allylation of in situ generated β,γ-unsaturated aldehydes affords rapid access to vinyl halide analogues of fragment A of the cryptophycins. Three scaffolds are prepared in gram quantities by a ring-closing metathesis approach. Derivatization via a variety of cross-coupling protocols is possible, which affords novel analogues of these potent antimitotic agents.

Total synthesis of cryptophycins. Revision of the structures of cryptophycins A and C

The convergent total synthesis of cryptophycins C and D is described. It has been shown that in both natural products the absolute configuration of the α-amino acid corresponds to the D-series. The structural assignment for cryptophycin C has been correct