99310-01-7

Basic information

• Product Name: N-Boc-N'-benzyloxymethyl-L-histidine
• Synonyms: N-ALPHA-BOC-NIM-BENZYLOXYMETHYL-D-HISTIDINE;N-ALPHA-T-BUTOXYCARBONYL-N-PI-BENZYLOXYMETHYL-D-HISTIDINE;BOC-D-HIS(3-BOM)-OH;BOC-D-HIS(BOM)-OH;BOC-D-HISTIDINE(3-BOM)-OH;BOC-D-HIS(PI-BOM)-OH;BOC-N-P-BENZYLOXYMETHYL-D-HISTIDINE;nα-boc-π-bom-d-histidine
• CAS NO: 99310-01-7
• Molecular Formula: C19H25N3O5
• Molecular Weight: 375.42
• Product Categories: Amino Acids
• Mol File: 99310-01-7.mol

Chemical Properties

• Boiling Point: 595.3oC at 760 mmHg
• Flash Point: 313.8oC
• Appearance: White to off-white/Powder
• Density: 1.21g/cm3
• Vapor Pressure: 5.11E-15mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: -15°C
• CAS DataBase Reference: N-Boc-N'-benzyloxymethyl-L-histidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-N'-benzyloxymethyl-L-histidine(99310-01-7)
• EPA Substance Registry System: N-Boc-N'-benzyloxymethyl-L-histidine(99310-01-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 99310-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-N'-benzyloxymethyl-L-histidine is used as a reactant for the synthesis of Land D-amino acid sequences in the preparation of snow flea antifreeze protein. This protein is of interest in the pharmaceutical industry due to its potential applications in the development of treatments for cryoprotectants, anti-freeze agents, and other therapeutic agents that require protection against freezing or cold-related injuries.
Additionally, the compound may be utilized in the synthesis of other bioactive peptides and proteins, given its unique structural features and reactivity. Its use in the pharmaceutical industry highlights the importance of innovative chemical compounds in drug discovery and development processes.

InChI:InChI=1/C19H25N3O5/c1-19(2,3)27-18(25)21-16(17(23)24)9-15-10-22(12-20-15)13-26-11-14-7-5-4-6-8-14/h4-8,10,12,16H,9,11,13H2,1-3H3,(H,21,25)(H,23,24)/t16-/m1/s1

Upstream product

• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 20898-43-5 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 83468-80-8 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine methyl ester hydrochloride 
• 79950-77-9 N^α-tert-Boc-N^?-<(benzyloxy)methyl>-L-histidine methyl ester 

Downstream Products

• 83468-96-6 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-N(?)-benzyloxymethyl-L-histidine methyl ester 
• 83468-95-5 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-N(?)-benzyloxymethyl-L-histidine methyl ester 
• 6858-60-2 cyclo-(Leu-His) 
• 79950-74-6 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-L-phenylalanine methyl ester 

Relevant articles and documents

N-HETEROCYCLIC ALCOHOL DERIVATIVES

Compounds of the formula STR1 wherein R 1 is an N-heterocyclic group as defined herein, are disclosed. These compounds are inhibitors of renin and therefore useful as cardiovascular agents.

Further Studies on the Protection of Histidine Side Chains in Peptide Synthesis: The Use of the ?-Benzyloxymethyl Group

Further studies on the use in peptide synthesis of N(?)-phenacyl protection for histidine side chains have shown that whilst this prevents the side chain-induced racemization which can occur if there is a lone pair of electrons available at the ?-nitrogen, there are concomitant drawbacks.As an alternative approach to the racemisation problem, the effect of halogenation of the heterocyclic ring carbons (to diminish the availability of the ?-nitrogen lone pair) has been investigated.This gives derivatives which are convenient in both classical and solid-phase applications, the halogen modifying groups being removed at the last stage by catalytic hydrogenolysis over a rhodium catalyst.Racemization is suppressed as expected, but it is not eleminated completely: direct blockade of the ?-nitrogen appears to be indispensable for its complete prohibition.Protection of the ?-nitrogen with a benzyloxymethyl group has now been found to be much more satisfactory than the use of the phenacyl group for this purpose.A ?-benzyloxymethyl substituent not only prohibits side chain-induced racemisation but also gives derivatives with convenient physical properties which can be incorporated into well estblished classical and solid-phase strategies without the need for any novel or additional operations or changes in protocol.The protecting group is stable to basic conditions, to trifluoroacetic acid, and to aqueous solutions of carboxylic acids, but is cleaved cleanly and rapidly by hydrogen bromide in trifluoroacetic acid or by catalytic hydrogenolysis.N(α)-t-Butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine has been prepared in good yield by a simple procedure from an easily accessible intermediate and isolated as a crystalline solid; its use has been demonstrated by a number of exercises including a solid-phase synthesis of 5-isoleucine-angiotensin II and a classical synthesis of trihistidine.

Protection of Histidine Side-chains with ?-Benzyloxymethyl- or ?-Bromobenzyloxymethyl-groups

N(α)-t-Butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine (1) and N(α)-t-butoxycarbonyl-N(?)-4-bromobenzyloxymethyl-L-histidine (2) have been prepared and shown to be suitable derivatives for peptide synthesis with histidine; the synthetic intermediates had