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Human beings have been using natural products since the dawn of human history. Throughout the ages, Nature has provided man with sources of the essentials of life, including food, medicines and other raw materials necessary for the sustenance of life. Plant products form a very large group of natural products including compounds from the animal kingdom. The term natural product is normally used to denote organic compounds of natural origin, often with complex structures, which are unique to one organism or common to a small number of closely related organisms and in most instances they appear to be non-essential to the organism, for example morphine produced by the poppy plant or penicillin present in some species of fungi. The study of the chemistry of natural products has attracted chemists since very early times of scientific inquiry but the first isolation of a pure alkaloid, morphine by Serturner, only occurred in 1805. Out of such scientific investigations during the last two centuries, many useful products such as therapeutic agents, dyestuffs, essential oils, vitamins, hormones, etc have been obtained. The complexity of such structural and synthetic studies can be appreciated by noting that the structure of morphine was solved after more than a century of study in 1925 by many early eminent researchers and its first total synthesis was achieved only in 1956. These investigations have also been the principal driving forces for much
Editorial Committee Editor: Lee Hian Kee Co-editor: Chin Wee Shong Members: Chan Kwai Sum Teo Ming Ern
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present in the roots of the plant in small amounts and was not suitable for economic exploitation. Another interesting result was his study of the constituents of Kopsia singapurensis which yielded three new alkaloids with very novel structures related to the periwinkle alkaloids vincristine and vinblastine used in leukaemia chemotherapy, and to which he gave the names, kopsingine (I), kopsaporine (II) and kopsingarine (III), with the Singapore flavour. His findings resulted in characterisation of numerous interesting natural products which were published in over thirty papers. This was a very commendable effort considering that research funding was practically non existent and research students were a rare species very hard to come by. During his career he had a total of less than ten research students and four of them who studied under him on natural products continued on such work and eventually went on to head the departments of Biochemistry and Chemistry at the University of Malaya and the departments of Pharmacy and Chemistry at NUS.
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Dr Chin Wee Shong Chemistry Alumni Network Department of Chemistry National University of Singapore 3 Science Drive 3, Singapore 117543 Email: chmcws@nus.edu.sg
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Specials
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the Department of Chemistry at the Nanyang University. He gave much support and encouragement to the staff and students and helped bring about a smooth merger of the two Chemistry Departments when the National University of Singapore was formed in 1980. He finally retired from academic life in 1980 at the age of 65. Prof Kiangs main research interest was in the chemistry of organic heterocyclic compounds and natural products occurring in plants and animals. The latter covers a wide range of topics in organic chemistry, viz. foodstuffs and agricultural products; physiologically and pharmacologically important compounds; constituents of cells in lifes reproduction processes like nucleic acids, RNAs and DNAs, etc. which are fundamental to the study of life sciences. In spite of the heavy duties as administrator, teacher and research scholar, Prof Kiang was also very active in public and social services. He was a founding member of a number of clubs and associations, such as the Gan Eng Seng School Old Students Association, the Singapore National Institute of Chemistry, the Singapore Institute of Food Science and Technology). He is also one of the oldest members of the National University of Singapore Society. For his service to many other societies and organizations, he was awarded the Pingat Bakti
new dimension. Natural product research has always been closely linked with the life sciences and natural product research for the discovery of novel and more effective therapeutic agents will continue to be one of the major approaches in the drug discovery programme of pharmaceutical companies and other research organisations for there is nothing more important than Life itself. In Singapore, the EDB and GlaxoWellcome had already in 1993 contributed $50 million to set up the Centre for Natural Product Research (CNPR) with the aim to develop and operate high throughput screens for the discovery of biologically active molecules from natural sources
Masharakat (Public Service Medal) by former President Dr Wee Kim Wee in 1987. Prof Kiang has made his mark in Singapore and in the scientific world. He has given unreservedly of himself in 33 years of devoted service to Raffles College and later to the University. His very person and extensive contributions has inspired many and we are glad that the Kiang Ai Kim Scholarship Fund has been established in NUS to honour his contributions to the Chemistry Department as well as to the progress of Chemistry in Singapore and the region. A committee chaired by our alumnus Mr Wong Ah Long, CEO of Suntec City Development Pte Ltd, has been set up to raise $500,000 for the Fund. The objectives of the Fund include (1) To award scholarships and book prizes to encourage outstanding students to read Chemistry at the University (2) To recognize deserving Chemistry undergraduates, and (3) To develop faculty, staff and students, in line with Prof Kiangs work in the chemical industry. We at the NUS-Chem Alumni Network is very glad to be involved in intializing and supporting the setting up of this Fund. We wish to encourage our alumni to contribute to this Fund as a tribute to Prof Kiang as well as for good course of supporting the objectives of the Fund. Contact Joyce at 874-6361 or chmcsk@nus.edu.sg for more details.
which can serve as leads for drug development. CNPR is located in the Science Park and expands the scope of pharmaceutical activities in Singapore beyond manufacturing into cutting edge research and development. Drug discovery is, however, a very slow process and a very capital-intensive undertaking (US$200-300 million per drug) and it may take as long as ten years before a drug becomes clinically useful from the time of its initial discovery. It is also a knowledge-intensive industry and as advances in many life-related phenomena can only be understood or clarified on a chemical basis, natural product research will continue to be an important bridge between chemistry and the life sciences. ChemConnections 3
Specials
Emeritus Professor Kiang Ai Kim: A students reminiscences and appreciation - by alumnus Dr Loke Kwong Hung
I was among the first batch of Preliminary Year science students admitted into the University of Malaya. After a term test evaluation, two others and I were promoted into the Intermediate Year. In the sessions 1950-51 (Year II) and 1951-52 (Year III; Pass Degree Year) I read Chemistry, Physics and Pure Mathematics, with the objective of specialising in Chemistry or Physics in the Honours Year. As I remember it, it was in 1952 that we were taught by Professor Kiang in organic chemistry, a major topic he lectured is the chemistry of heterocyclic compounds. The organic chemistry of the Honours Degree course then was taught by three lecturers: Dr. Rayson L. Huang, Dr. Kiang Ai Kim and Dr. Leong Peng Cheong. All three subsequently left their mark on chemical or biochemical education in Malaya and Singapore. Dr. Huang lectured on free radical chemistry and steroids, Dr. Kiang on the chemistry of plant natural products with particular reference to alkaloids and antimalarials, while Dr. Leong on the chemistry of nutrition and vitamins. While physical and inorganic chemistry were just as effectively and interestingly taught in the course, to me organic chemistry proved a greater attraction. Through the lectures of the aforementioned three lecturers, I became interested in the relationship between chemical structure and biological activity, which in turn led me to yearn for knowledge on the chemistry of life (biological chemistry or biochemistry). My aspiration then was to win a scholarship to enable me to study biochemistry in an overseas university. (Biochemistry was only taught to medical students in the local university at that time). It naturally followed that with the appointment as Demonstrator I pursued research in organic chemistry for my MSc Degree. Thus I became Professor Kiangs first research student. In briefing me about my research programme, he mentioned that he and coworker had isolated a known cyclitol dambonitol - from rubber latex. Previous work showed that it is a di-O-methyl derivative of inositol but its precise structure was unknown. The periodate oxidation studies on dambonitol showed two moles of periodate were consumed per mole of cyclitol oxidised, a result consistent with the 1,4-dimethyl inositol or 2,6-dimethylinositol structure. However, the titratable acidity in the periodate oxidation experiment was found to be about 0.2 molar equivalent per mole oxidised, a result not consistent with either structure, as the expected yield would be zero or one molar equivalent respectively. Therefore, my research objective, he said, was to identify the dialdehyde formed in the periodate oxidation. The dialdehyde is water-soluble, an attempt was therefore made to isolate it in the form of its phenylhydrazone derivative. The reaction product I got was an oil. A novice as I was then, I could not get it to crystallise. Professor Kiang took over. After addition of some solvent he chilled the mixture and started to scratch the oily mixture with a spatula against the study with titrimetric analysis of acid liberated gave a curve plateauing at the expected stoichiometric yield. The year I spent in Professor Kiangs laboratory had been fruitful not only in the discovery of new knowledge but also in my acquisition of various skills that would stand me in good stead in facing the challenge of doctoral research in biochemistry at the University of Edinburgh. For example, the technique Professor Kiang used to coax crystals out of a seemingly intractable oil was applied successfully in my isolation of crude oestrogen metabolites from concentrates obtained from 8001000 litres of human late pregnancy urine. During the period of my M.Sc. research Professor Kiang had at least two other projects going on too. One was concerning with the investigation of organic extractives from sawdust. His assistant, Mr. Jimmy Goh, would pack a large distilled water dispenser with saw dust, attach a condenser with side-arm, through which boiling solvent vapour would enter and condense to give the warm liquid solvent which in percolating through the saw dust would extract certain components. Portions of the percolate would then be withdrawn for work-up. What I saw then was an improvised Soxhlet-type extraction apparatus, albeit being operated batchwise. I learnt a lesson then, viz. do not wait for equipment to be acquired and let precious time pass by; improvise with what you have and get the research moving. The other project was the isolation and identification of the active principle(s) of chilli (capsicum). One of the steps in the isolation was steam distillation of a homogenate of the chilli and to locate the principle in the distillate, Professor Kiang would dip a glass rod into a distillate fraction and let the liquid adhering to the rod drop on his tongue. By this monitoring procedure, he would know which distillate fraction would contain the active principle. However, with repeated testing blisters began to form on his tongue. While feeling sorry for his pain and discomfort, I nevertheless admired his grit and dedication to research. His spirit and action exemplified the Chinese saying: If we do not enter the tigers den, how are we to get the cub?
Dr Loke Kwong Hung was born in 1927 in Kampar, Perak. He was among the first batch of science students in the University of Malaya in 1949. After obtaining his BSc (First Class Honours) degree in 1953, he pursued his MSc study under the supervision of Prof Kiang at the University. He was later awarded the Queens Scholarship to pursue his PhD at the University of Edinburgh. Dr Loke was appointed a lecturer in Biochemistry at the University of Malaya in Singapore in 1958. He has since served as a Lecturer, Senior Lecturer, Professor and Head of the Department of Biochemistry in the University of Malaya in Kuala Lumpur. He has also served as a Senior Teaching Fellow at NUS (1982-1988) and was a Research Consultant of the Palm Oil Research Institute of Malaysia (PORIM, 1988-1994). His field of specialization is in steroid biochemistry with particular reference to urinary oestrogen metabolites and metabolism of androgens and oestrogens by human placenta and porcine adrenal.
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I met Professor Kiang again in late 1958 when I completed my Ph.D. studies and returned to Singapore to take up my lectureship appointment at the Department of Biochemistry in the Faculty of Medicine, University of Malaya. Later, upon my election to the post of Hon. Secretary-Treasurer of the Malaya Section of the Royal Institute of Chemistry (RIC) London, I served under Professor Kiang, who was Chairman of the Management Committee. The RIC Malaya Sections main objective was to promote chemistry and professionalism among its members and was prominent in these roles during colonial times. However, with political changes taking place in the region covered by the Section, RIC members from both sides of the Causeway held discussions to remodel the Section to suit the new circumstances. In these deliberations Professor Kiangs views and counsel proved useful. Since 1964 when I left Singapore to take up a lecturer appointment with the Department of Biochemistry of the newly established Faculty of Medicine in University of Malaya, I was unable to meet Professor Kiang as much as I would like. Therefore on occasions such as the major functions of IKM (the Malaysian Institute of Chemistry) which we happened to attend, I was very glad to see him hale and hearty and as enthusiastic on things chemistry as before. Last October I attended the celebration of the 50th anniversary of the University of Malaya (UM) held by the National University of Singapore, of which UM is its precursor. At the reception held before the Reunion Dinner on 8 October I saw Professor Kiang entering the hall and went forward to greet him. So did several others of his former students and soon he was surrounded by us all. When he mentioned in passing that in recent times he felt weakness in his legs, one of us quickly went to fetch him a chair to sit on. Such is the depth of respect and concern we his
former students have for him. This May, the Science Faculty of the National University of Singapore celebrated i 70th anniversary and the Millenium. t s On 27 May I attended the public lecture by Lord George Porter, FRS, Nobel Laureate and I met Mr. Lim Ho Hup, my fellow student in 1949-1954, at the foyer of the lecture hall. When we entered the lecture hall, we saw Prof Kiang seated among the front rows. We went over to greet him. After the lecture, the three of us had lunch at the Guild House. Apparently Prof Kiang had enjoyed this unplanned reunion with us very much, as he invited us home to continue the conversation. We talked on a variety of topics including Chinese culture and literature. Ho Hup wrote a Tang Dynasty poem down to illustrate a point. Seeing the calligraphy executed with a ballpoint pen prompted Prof Kiang to show us his Chinese brush calligraphy. We were
impressed by its quality. When he told us that he had taken up calligraphy lessons two to three years ago, we were the more impressed by his achievement. I was glad that after an active career in chemistry he has developed other interests such as gardening and calligraphy. For, according to experts, calligraphy can bring benefit to ones body and soul. At the Gala Dinner on 28 May I was delighted to find myself seated at the same table as Prof and Mrs. Kiang and staff members of the Department, most of whom I have known since the fifties. How thoughtful of the organisers of the dinner in making such a seating arrangement for me! I am thankful to the Editor of ChemConnections for the invitation to provide some words on Prof Kiang. For, this gives me the opportunity to express my appreciation of him as a fine scholar, an inspiring teacher and mentor and a humble, sincere and caring person. And, to wish him a Happy Birthday, continued good health and bliss with Mrs. Kiang.
Nanosensors
Technologies have also been developed for the preparation of nanofilms for chemical immunosensing and DNA sensing. In addition, nanoscale analytical techniques have been developed and commercialised for high resolution separation of DNA, proteins and drugs. Refreshments will be served.
Workshop details:
Date: Saturday, 24 February, 2001 Time: 9.00 am - 13.15 pm Venue: NUS,,Block S16, Level 3,,LT31. Cost: $25 non-SNIC member, $20 SNIC member. Registration by Saturday 3 February 2001 to Dr Ryan P.A. Bettens, Department of Chemistry, NUS. Email: chmbrpa@nus.edu.sg
The 10-storey Science Tower built at the Bukit Timah campus to accommodate the Chemistry Department stands as a constant reminder of Professor Kiangs devotion to the cause of scientific education in Singapore
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Department News
Newcomers ...
Dr Ryan P.A. Bettens is an Australian who grew up in Redcliffe, a town about 30km north of Brisbane, Queensland. He received his B.Sc. from the University of Queensland, and from there moved to Melbourne to study for his Ph.D. at Monash University. His Ph.D. research involved interstellar chemistry (i.e. chemistry in space) and microwave spectroscopy (a spectroscopic technique used to study the rotational motion of molecules and complexes and provides detailed information on their structure and dynamics). He carried out his post-doctoral research for about 8 years at the ETH, Zurich, Switzerland; Ohio State ChemConnections 6
two numbers: a Mandarin evergreen and the theme song from Journey to the West, a hit TV series from China some years ago. The contribution of the Department of Chemistry to the proceedings was Prof Lai Yee Hings perennial favourite: a magic show, based not on sleight of hand but on the principles of chemistry (see photograph). On a more cerebral note, Dr Lim Saw Hoon of the Department of Biological Sciences, presented a half-hour talk A Glimpse Into Genetics. As a follow up to the talk, there was a tour for the visitors to the Raffles Museum of Biodiversity Research and a Poster Corner, where visitors gained interesting insights into the biosciences. A Science Quiz whose answers could be found in the Poster Corner and in the talk saw participation from both children and adults. After a tea reception, Prof Lai Choy Heng presented the three top winners of the quiz with attractive prizes. It was indeed a memorable and enjoyable time for all present.
Introducing Staff of the Food Science and Technology Programme in the Department of Chemistry
Food is always an important matter to Singaporeans, but it did not have a specific academic programme in the University until a new major in Food Science and Technology was introduced last year. This programme aims to develop the particular skills and knowledge in graduates who would primarily find their future careers in the modern food and beverage industry. With the great variety of foods that the modern consumer expects, the modern food production industry is sophisticated and high tech and requires graduate-level staff to manage and control it. The four-year honours programme, whilst based in Chemistry, crosses the Faculty barriers and gives the students knowledge and skills across a range of disciplines. Currently the dedicated staff for the programme are all based in the Department of Chemistry but comprise a small team which is anticipated to grow to 10 or 12 members over the next few years. Of the five members of the team, two are old hands from the University and three are relatively newcomers. Members are Prof Lee Cheang Kuan (who many of our alumni know), Assoc Prof Philip J. Barlow, Assoc Prof Conrad O. Perera Dr Leong Lai Peng, all well supported by a dedicated technical officer Lee Chooi Lan (ex-Department of Biological Sciences).
The photograph shows members of the FS&T programme: (from left to right) A/P PJ Barlow, Prof CK Lee, A/P CO Perera and front row, C.L. Lee and Dr L.P. Leong
The Food Science and Technology Programme is underpinned by appropriate research and the main areas of activity by the staff are as follows:
Prof Lee Cheang Kuan: Chemistry of monosaccharides and disaccharides Sucrose is probably the most widely used sweetener in foods. Its sweetness is, however, relatively low compared to sweeteners such as saccharin, but there is now an intensely sweet synthetic analogue of sucrose, sucralose (or 4-chloro-4-deoxy-a-Dgalactopyranosyl 1,6-dichloro-1,6dideoxy-b-D-fructofuranoside) (650 times that of sucrose or more than twice as sweet as saccharin), available in the market. This sweetener has just received approval of the US Food and Drug Administration for use as a high intensity low-caloric sweetener in f oods. The research interest in this area is directed towards finding the extent to which chemical principles apply to phenomenon associated with the inductive (recognition) phase of taste. The study also aims at determining the relationship between chemical/stereochemical characteristics and intensity of sweetness, which could help to predict the probable nature of the recognition chemistry for the sweet taste. A/P Conrad Perera: Chemistry and technology of processing horticultural crops The major area of emphasis is on the effects of processing on fruit juice quality and the stabilisation of colour, flavour and texture by minimal processing of foods There is increasing demand for minimal processed foods having adequate safety and shelf life. The research includes the application of modified atmosphere packaging, edible coatings and pre treatments to minimise microbial contamination which leads to product deterioration. A/P Philip Barlow: Nutrients and contaminants in food as regards food safety There is increased interest in the composition of foods as regards health. Foods no longer just have to be safe to eat but should contribute to positive health and hence, the development of functional foods. Research is focussed on examining foods for contamination and also their nutritional composition so as to provide optimal nutrient intake for disease prevention. Interactions between components which affect their bio-availability is an important aspect of the work.
Dr Leong Lai Peng: Indigenous foods as sources of functional food development South-east Asian is an area rich in fruits and vegetables and there are many opportunities to develop some of these as functional foods. The research is exploring the composition of foods and relating the structure of components to potential health benefits. Also the research is looking at how some common food reactions (e.g. Maillard reaction) produce compounds that are beneficial as regards stability and improved quality of foods. These natural products find favour in applications in other foods and reduce the need for artificial additives.
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Alumni News
Chemistry Night
Friday, 9 February 2001, 6:309:30 pm Raffles Town Club, 1 Plymouth Avenue Dress code: Smart casual
The Department of Chemistry and the Singapore National Institute of Chemistry, the professional body in Singapore representing the interest of chemists and chemistry, are pleased to work together to Department has bring the chemistry community to produced, the vigor Raffles Town Club for a social of our training evening. This is an opportunity to program and the rekindle and strengthen relationrelevance of our research projects to ships, and meet old and new the local engineering friends. The Chemistry Night ofindustry. It is also a fers a relaxed atmosphere for us testimony that scientists adapt very to mingle and chit-chat, and an inwell to the demands of the electronic formal occasion to establish netindustry. We have quite a number of work links and professional consuch graduates in the industry, many tacts.
of them are working as engineers, Dr Liu is a fine example of such. Congratulations, Dr Liu!
The cost is $45 per person (inclusive of light dinner and drink) but SNIC members and NUS Chemistry Alumni only pay a subsidised rate of $35. An early reply, definitely by 15 January 2001, is essential, for catering purposes. For enquiries, please contact Dr Chin Wee Shong at her email chmcws@nus.edu.sg, or Ms Joyce Chor (Tel: 874-6361).
salts. I guess the best part of the ceremony would be the photo taking after the conclusion of the ceremony. I went trigger happy, snapping at every opportunity. In fact, I ran out of film halfway. Looking back at these photos as I write, familiar faces make me smile and chuckle to myself as I recall the many wonderfully hilarious moments I had with these great friends. What makes this ceremony especially memorable is the fact that we went through a gruelling course together and this common experience somehow bonds us together. I look forward to the next class gathering to relive the happy moments and share the tough ones. Teo Ming Ern Chemistry Honours 2000